


Whiskey's Son

by pm_lo



Category: Supernatural
Genre: Alternate Universe - Human, Antagonism, Enemies, Harlequin, Love/Hate, M/M
Language: English
Status: Completed
Published: 2014-07-09
Updated: 2014-08-02
Packaged: 2018-02-08 03:13:41
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 8
Words: 27,090
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1924590
Author URL: https://archiveofourown.org/users/pm_lo/pseuds/pm_lo
Summary: <blockquote class="userstuff">
              <p>Young heiress Anna is in danger of throwing her fortune away on a low-life bartender. Her brother Castiel is dispatched to make sure this <em>does not happen</em>.</p>
            </blockquote>





	1. Chapter 1

**Author's Note:**

> This is an adaptation of the amazing Georgette Heyer’s [Faro’s Daughter](http://www.amazon.com/Faros-Daughter-Georgette-Heyer-ebook/dp/B001P5043M/ref=sr_1_1?ie=UTF8&qid=1404890982&sr=8-1&keywords=faro%27s+daughter), which you should all go read _immediately_. (Unless you want to remain unspoiled for this story.)

He wasn’t the Roadhouse’s usual customer, that was for sure.

The suit meant he could’ve afforded the swankier bars in the better part of town - most of the Roadhouse’s customers worked construction, if they worked at all. There was nothing particularly creepy or off-putting about him, so he wasn’t there trying to scam on what he thought was more vulnerable game. And though he approached the bar warily, scanning the room, he didn’t seem to be meeting anyone.

When he finally sat down and caught Dean’s eye, he revised his earlier opinion - there was a _little_ creepy going on. A soupçon. 

And his opening request didn’t exactly set Dean’s mind at ease: “Are you Dean Winchester?”

“Uh,” Dean said, glancing down at his chest just to confirm that he did not, in fact, wear a badge. With his last name. “Yeah, that’s me. Have we met?”

“A friend recommended this place,” the man said. “Said you make the best burgers in town.”

“Your friend’s right,” Dean said reflexively, but then: “He mentioned me by name?”

The man frowned, and Dean cursed internally - creepy or not, this guy clearly had cash to drop, and him just being here was enough of a miracle for Dean to put up with _whatever_ his deal was. “I’ll bet you want to try one, right?” He asked, with his flirtiest grin.

The man looked taken aback, but said only, “Yes.”

When the order was ready Dean was happy to drop it off and leave Creepy Esquire with nothing more than a wink and a smile, but he was stopped by a flat, gravelled, and unexpectedly earnest: “I’m sorry.”

Dean blinked. “For what?”

The guy spoke like he was announcing scientific facts, not conversing with another human being. It was weird. “I made you uncomfortable.”

“Uh, no, no you didn't,” Dean said. He would have darted away, except the only excuse he could use was Zachariah waving at him from the other end of the bar, and he would honestly rather get to the bottom of what was up with Eerie McUndeniably Hot. Plus the guy _did_ seem sorry, so Dean smiled at him, genuinely this time, and nodded toward the burger. “So what’s the verdict?”

He started as if he’d completely forgotten about his order, then took an enormous bite of the burger - and Ellen didn’t serve no sliders. Dean whistled in appreciation and grinned at the combination of the guy’s intently serious face as he chewed and the chipmunk-cheek effect.

“Not bad,” he eventually said, when he had gotten the chewing down to a minimum.

“Not bad?!” Dean protested. “Dude, no. Where have you ever gotten a better burger?”

The man shrugged, looking a bit sheepish, took another bite, then said, “It’s very good. I’m just used to more... modern cuisine.” _No shit._ “It’s been a while since I went to a bar.”

“Honestly,” Dean said, “You look like it’s your first time.”

The man’s full lips quirked in a tiny grin. “I assure you, it’s not.”

“Oh yeah?” Dean teased, leaning against the bar. “You were a real lush back in the day?”

That earned a suspicious squint instead of a return volley, which just made Dean laugh. “In fact, I was,” the guy replied.

“Prove it.”

The man stared at him, only the slightest hint of uncertainty flashing through his eyes before he said, “Five shots of vodka.”

Dean grinned. “Only five? Why not ten?”

The man narrowed his eyes, but said, “Very well. Ten.”

Dean barked out a laugh. “Okay, pal. But you throw up on my bar, you’re buying me a new one.”

He was still glaring as Dean laughed all the way to the booze. When he had the drinks lined up the man reached for the first without fanfare, but Dean grabbed his wrist before he could touch it. His skin above the cuff of his suit was hot.

“Hang on,” Dean said. “What’s your name? Y’know, for when I have to make my statement to the police.”

“Castiel,” the man said, and proceeded to down the shots as if they were water while Dean watched on in awe. When he was done he brushed a stray drop of vodka off his lower lip and said, “I’ll take another burger now.”

Dean whistled appreciatively and turned to put the order in through the window. “Okay, so you have been to a bar before, _Castiel_. Why the long absence?”

“I became... busy,” Castiel said, staring at the smooth wood surface of the bar.

“Lemme guess,” Dean said. “Family obligations?”

Castiel’s eyes snapped to his. “Actually, yes.”

It had probably been too long since he’d checked in with Zachariah or the few other customers, but Dean was enjoying his strange tete-a-tete with Castiel. “I hear you there,” he said. 

“You have a demanding family?”

“No, I mean, not _demanding_ ,” Dean said. “Just, y’know. Gas, ass, or grass, know what I’m sayin’?”

Castiel looked contemplative. “No.”

“I - nobody rides for free.”

“Rides where?”

Dean rolled his eyes. “I meant - life’s expensive. Taking care of your family, it’s an important job.”

“I agree,” Castiel said.

“So what’s your family’s deal?”

Castiel dropped his stare again, eyes moving restlessly around the bar. "I thought people came to bars to escape their troubles."

"Yeah - to unburden themselves to their friendly neighborhood bartender," Dean said, smiling encouragingly.

Castiel stared, unmoved.

Zach had started practically dancing in his seat at that point, so Dean shrugged and left to get him the slice of pie he’d taken to ordering because he’d heard Dean mention he loved it and of fucking course. Still, Dean gave him a wink as he set the pie plate in front of him, and Zach’s oily answering grin told him he’d repaired things enough to guarantee a big tip later. He could feel Castiel’s eyes on him from the other end of the bar. 

It was funny how when he’d first agreed to this he’d thought running a bar would be mostly pouring booze, doling out tips, and the occasional, unavoidable bit of math. Instead he spent most of the time feeling like a painted whore - smiling for the customers, remembering their bosses’ or pets’ names, teasing and flirting and doing anything he could to have them back the next night, order another drink, leave a big tip.

Anything to keep the place afloat.

"You seem troubled."

Dean startled - with his back to the bar punching orders into the POS, he’d forgotten it was Castiel right behind him.

"Hmm?” he said, turning around. “No, I'm all good."

“You look tired,” Castiel said. “And stressed.”

“Well that’s a shame,” Dean said, leaning on the bar and ignoring the stupid stab of disappointment from the jab at his looks. “Because most of my job is to look pretty for the customers.”

“Of course,” Castiel said. “Must be tough. Maybe the bartender needs to unburden himself to the friendly neighborhood lush?"

Dean laughed. "That's not the natural order of things."

Castiel looked him up and down, something assessing in his gaze. "I'm a fan of overthrowing the natural order of things."

Dean smiled again, feeling drawn in against his will. He glanced around then bit his lip. "Okay, pal - I'll play you for it."

Uncertainty shadowed Castiel’s face again. "Play me?"

"Darts," Dean said, nodding with his chin. "I win, you tell me your family drama. You win, I... unburden myself."

Cas raised his eyebrows. "You’re still interested in my background? Why?"

Dean shrugged. "Seemed interesting."

Castiel seemed to hunch in on himself before mumbling, "I’m afraid I... don’t know how to play darts."

Dean’s jaw dropped. "You've never played darts? What the hell kind of bars did you used to hang out in?"

Castiel’s smile was almost shy. "They weren't so much bars, as... castles."

"Okay, now we're definitely playing," Dean said, walking around the bar and grabbing Castiel’s wrist again before he could stop himself.

"But I didn't agree to your terms," Castiel protested weakly, trailing behind him.

"You'll pick it right up," Dean said, grabbing the darts and walking back to where Cas was standing, looking uncertain, in the middle of the room.

“Here,” Dean said, grabbing one of his hands, ignoring that instinctual jolt of _skin_ , and closing it around a dart. “Just aim for the bullseye. Easy, right?”

Castiel stared at the dart, then Dean, then the board, and seemed to take a moment to steel himself. He raised the dart, aimed, threw - and a nearby saltshaker shattered as it shot off the table onto the ground.

“Holy shit,” Dean said, doubled over in laughter. He couldn’t even care about the mess or the loss in inventory. “This is gonna be too easy.”

“You tricked me into this,” Cas fumed.

“No, no, Cas, it’s okay, here -” Dean stepped forward, pressing another dart into his hand and then stepping behind him, using one hand to show Cas how to arc his shot properly and the other to tilt his body in the right direction. This time he hit the corkboard, not even the scored part, but his face lit up like a Christmas tree and Dean’s heart slammed in his chest. 

“That was better!” Castiel said, the dance of light in his eyes almost like a child.

“Exactly,” Dean murmured. “A few more practice shots, and you’ll be good to go.”

Cas turned back to the dartboard determinedly, and as he practiced Dean glanced up over his shoulder to see Zach watching them with a thunderous look on his face. All at once he realized what he must look like, spooning Cas like every romantic comedy cliche. He immediately tried to unobtrusively step backward, cool air sinking into his front as he distanced himself from Cas’s body heat. Cas didn’t seem to notice, making a few slow practice throws with the dart, but Zach just seemed angrier, hopping up off his barstool and actually walking over to them.

Until a dart appeared in the side of his neck, his eyes widened in comical shock for a moment, and he keeled over against the wall.

“ _Oh my god,_ ” Dean croaked, and rushed over to him. Zach was sputtering, seeming to switch between a dozen contradictory emotions as he fumbled for the dart in his neck. Dean lost about a year of his life in the split second before he got close enough to realize it hadn’t even pierced the skin, just gotten stuck for a moment before falling off. A lawsuit, that would have been _exactly_ what the bar needed.

“Zach, man, I am so sorry,” he said, deciding to steel himself and rub at Zach’s neck for, like, a second before yanking his hand away. It was the least he could do.

“I -” Zach started, but he saw something over Dean’s shoulder that stopped him, and before Dean could turn around to see what it was, he heard it.

“ _Cas?!_ ” Shrieked a feminine voice, and Dean turned in a daze, because it sounded like Anna, but that wouldn’t make any sense unless -

Anna was standing in front of Cas, who looked still shell-shocked by the whole darting-Zach incident, running her hands over his arms and gaping at him. “What’re you doing here?”

“I heard you loved this place,” Castiel said, slowly, like he was uncertain of his own words. “I wanted to see what all the fuss was about.”

Dean only had so much RAM in his head, so he decided to process things one at a time and turn back to Zach. “Seriously, are you okay?” he asked.

“Of course,” Zach said, drawn up back into his usual uptight self, something dark flitting behind his eyes. “Barely a nick.”

“Okay. Well next round’s on me, okay man?” Dean said.

Zach accepted, ungraciously as always, and by the time Dean had made his way back to the bar, Anna and Cas were sitting next to each other and Anna was fairly vibrating with excitement. When he got close she perked up in her seat and chirped, “Dean! Hey!”

“Hey.” He leaned over the bar to give her a kiss on the cheek.

She blushed, as usual, but then turned to frame Cas with her hands and said, “Dean, this is my brother Cas!”

_Oh._

It should’ve been obvious - rich, out of place, kind of an asshole: clearly a Raven. He was around Dean’s age, which would’ve made him at least ten years older than Anna, but that happened; they also looked _nothing_ alike - although Dean could see a bit of a resemblance in the sheer energy both had behind the eyes. Unlike Anna’s, though, which was exuberant and bubbled over, Castiel’s was leashed - like an attack dog.

It would have been stupid to feel like he’d lost something.

“Anna’s brother, huh?” Dean said, after the pause had drawn out slightly too long. “She’s one of our favorites.” Anna beamed.

“Then you have good taste,” Castiel said mildly. Maybe it was just in Dean’s head now that he knew who he was, but he seemed quieter than before, more shut-off.

Recalibrating toward why he must be here, Dean poured Anna her usual, waving the soda nozzle a bit obviously. Castiel saw but didn’t seem to react. Anna even backed him up, adding wistfully, “Only a few months until I can get a real drink!”. At that, Castiel’s face - darkened. _What?_

“But I love it here even without being able to drink - the food, the music. Plus Dean, of course,” she smiled. “He’s the best part of the Roadhouse.”

“So I’ve discovered,” Castiel said.

Dean laughed, which got frowns from Anna and Cas, because yeah, that was pretty weird. But he couldn’t help it, he found the fact that Cas had snuck in here on some kind of covert protect-sister-from-danger mission hilarious. And sad. 

He made sure they had everything they needed before making up some bull about leaving them alone to catch up, and went to hold court with the precious few other customers on the other side of the bar.

He had almost forgotten about the entire weird incident hours later, when he ran into Crowley in the hall leading down to the storage cellar. Crowley announced that he’d thrown out his back doing something something waggling eyebrows with a lady friend of his, so Dean would have to do the heavy lifting himself.

“Seriously?” Dean asked, though Crowley was already fleeing straight for the kitchen. 

“Seriously what?” He heard in a flat voice, and almost jumped before he remembered the bathrooms were back here. Castiel stood behind him, face shrouded in the shadows of the cramped hallway.

“Uh, Crowley,” Dean said, shrugging meaninglessly behind him. “One of my guys. Threw out his back doing something gross, so now I gotta lug the kegs up myself.”

“I’ll help you.”

Dean blinked. Cas didn’t exactly strike him as a physical work kinda guy, but the suit _was_ a little loose - maybe there were some muscles lurking under there. And that was officially enough time spent thinking about what Anna’s older brother looked like naked. “Aren’t you drunk, man?” he asked instead.

“No.”

Dean sighed and threw up his hands. “Sure, whatever.”

The basement was musty and dark even with the few lights on, and Dean warned Cas to be careful as they made their way down the narrow stairs. “This building is old,” Cas commented.

“Don’t I know it,” Dean groused. Repairs and maintenance took up _way_ too much of his time.

“Yet the bar is new,” Castiel said. Dean turned to him at the base of the stairs and frowned, because Cas sounded like he was waiting for some kind of explanation.

“Uh, what?” Dean asked.

“You bought the building recently?” Cas prompted.

“Bought? What - oh, no,” Dean said. “No, you’re right - the Roadhouse is new, but it was my Dad’s bar before that. He, uh -” Dean laughed, and rubbed the back of his neck. “It was called something different.”

“What?”

 _So much for social cues._ “Devil’s Trap,” Dean said, starting to survey the kegs to find the one he needed. “Not surprised you hadn’t heard of it, it was a rougher place.”

“I see.”

There were few things Dean wanted to do less than stand in a dank old basement talking about his fucked-up life to Anna’s older brother, but now that the anger was coursing through him he found himself talking again just to get it out. “Dad doesn’t have the best head for business. And I mean, alcoholic running a bar, never a good combo, right?” Cas said nothing. “When I realized how bad it had gotten I moved out here, convinced him to give it to me, roped my Aunt Ellen into helping out, and we re-opened as the Roadhouse. Serve food with the booze, less biker gangs.” He turned to look at Cas again. “You don’t have to worry about your sister hanging out here. It’s a good place, and Ellen and I always keep an eye out for her.”

“Moved from where?”

Dean had whiplash from Castiel’s scattershot approach to conversation. “What?”

“You said you moved here. From where?”

“Cicero,” Dean said, suddenly done indulging Cas’s whims. He pointed to a keg. “You think you can carry that one?”

Anna looked almost suspicious when Dean and Cas reappeared in the dining room, and her frown deepened when she realized they’d been together. But before she could say anything, Cas said, “It’s getting late. Anna, may I walk you home?”

“Oh.” Her face fell somewhat. Dean certainly wasn’t going to mention that Anna stayed later than this most nights.

“What?” Castiel asked.

“Yes, sure,” Anna said. “Let me just pay my check.”

“Of course not,” Castiel said, a credit card materializing out of nowhere. “Dean, could you charge both of ours, please?”

“Cas -” Anna protested.

“You introduced me to one of the best burgers I’ve ever tasted,” Castiel said, facing Anna, for which Dean was grateful so that his expression wasn’t noticeable. “I insist.”

Anna flushed with pride at the compliment to her taste and let Dean settle their bill. She did, however, tell Cas that she’d catch up with him when he slid his wallet back into his pants pocket. With a look between them Dean couldn’t decipher, Castiel left them alone at the bar. But Dean knew he was watching when Anna leaned over the bar to give him a quick kiss - aiming for his lips and getting his cheek, as usual.

Zachariah had a particularly cold look in his eye as Anna bounced out of the bar happier than Dean had seen her in a while. The tension in his chest was like a physical thing, a vice pulling at his muscles and bone until he felt like he was going to snap. 

Just another night at the bar.

*

Anna glanced over at Castiel as they walked arm in arm, the streetlights casting harsh shadows on his angular face, and wondered how he could look exactly the same as when she had last seen him almost a year ago. Her own life felt as if it had changed so much since then, and yet here was dear old Castiel, still with the ruffled hair, the closed-off eyes, the deadpan face.

“I could have sworn Naomi sent you,” she said, watching that face closely. 

It was unperturbed. “When have I ever been Naomi’s errand-boy?”

“You have been toeing the company line lately,” she said, giving his suit a disdainful once-over.

“Even rebellion becomes meaningless after a while,” he said calmly, though his tone made Anna hunch closer, suddenly cold. “Doesn’t mean I’m one of them.”

“You’re right,” she said, giving his arm a squeeze. “I shouldn’t have doubted you. In fact, maybe you’ll be able to help me.”

“Oh?”

She smiled even more brightly. “Isn’t the Roadhouse wonderful?”

“The burgers are very good,” Castiel said. “I’m not sure about the clientele.”

“They do get a creep now and then,” she conceded. “But it’s so vibrant, so - alive! The people are friendly, and they don’t care who you are or where you came from. Nothing like home.”

Castiel nodded his head in silent agreement.

“And the thing is,” Anna said, “it’s in trouble.”

Castiel frowned. “In trouble? How do you know?”

“Dean!” Anna said. “He puts on a brave face, but they’re struggling. The economy’s still terrible, and they have so much debt from when it first opened. So,” she said, injecting what she hoped sounded like wisdom into the word, “I want to invest in them.”

“Them?”

“The bar! Dean and his aunt Ellen.”

“Ohh,” Castiel said, the word uncoiling as something flickered across his face. “You and Dean, you’re... together?”

“No!” She immediately protested, feeling her face heat. “We - I mean, it’s - it’s complicated.” She sighed. “I think he just wants to take things slow. Since I’m, y’know, a little younger.”

Castiel’s face was impossible to read. “A little.”

“But that has nothing to do with this!” She urged. “I know it’ll be a profitable investment once they finally have some room to breathe. But I’m worried they won’t be able to hold out until my birthday.”

“Until you come into your trust,” Cas extrapolated.

“Yes! Two months is a long time, they could go under, or Dean -” She sighed. “He’s so stubborn, I worry about what he might do if things get bad enough.”

“Like what?”

“Like take out a bad loan. Or...” She hesitated. “Did you notice that guy tonight, on the other side of the bar? Older, pudgy, bald?”

Oddly, Castiel turned bright red and seemed to stutter for a moment before saying, “Uh, no.”

Anna decided to move past it. “Dean’s told me a little about him. He’s this creep who’s offered to invest in the bar, multiple times.”

“That sounds like exactly what they need.”

Anna ground her teeth. “No - he’d be investing in _Dean_. If you know what I mean.”

Cas made a satisfyingly disgusted face and a tiny, restrained _ick_ sound.

“And I don’t think Dean would ever do that,” she continued, “but he can’t tell the guy to fuck off, because he spends a lot at the bar. And if the bar goes under before I turn twenty one and Dean has to move away or - or do something drastic, I don’t know what I’d do!”

“Move with him,” Cas said. “If you really love him.”

Anna’s jaw dropped. “You don’t understand - the Roadhouse means so much to him! He’d be devastated if he lost it.”

“Then he probably wants it to succeed on its own merits,” Castiel said, voice still infuriatingly calm. Anna felt her temper flare.

“Whose side are you on in this, Castiel?”

It was always hard to stay mad at Castiel, especially when he had that blank, innocent face on, the one that said _why would I steal your comic books? I don’t even know what a spider man is_. “I’m on your side, Anna,” Castiel said. “I want you to make the best choice.”

Anna blew out a frustrated breath. “Well, I’ve tried explaining to Naomi that it’s time sensitive, but she - she’s horrified, she hates the bar - hasn’t ever been, obviously, just hates it on principle - and she _hates_ Dean. She thinks he’s beneath me, somehow, because he runs a bar instead of a company. But Cas, can’t you see how wonderful he is?”

“I can see why you like him,” Castiel said diplomatically.

Anna flushed. “I’m not just - I told you, it’s not like that, Cas, he’s just - will you talk to Naomi?”

“I’ll think about it.”

“Cas!”

“Tell me about school,” he said firmly, rubbing a hand over hers where it rested on his arm as they turned the corner.

*

Dean drummed his fingers on the table as he watched Ellen shuffle through receipts and punch numbers into her giant, old-school calculator. He’d make fun of her except the nusto steampunk system actually worked somehow, and Dean was almost as shit at numbers as his old man, so he’d learned to shut up.

The look in her eyes when they finally raised to his did not bode well. “That bad?” He asked, heart in his throat.

She sat back in her chair and rubbed her eyes. “We’re raking it in, just not fast enough. The debt your Daddy took on...”

“I know, I know,” Dean said, slumping forward to rest his head in his hands. “There’s nothing we can do?”

“Try to keep pace,” Ellen said. “But unless the Superbowl comes to town...”

“Fuck,” Dean breathed. He tried not to picture his Dad’s face. Sure, _Dean_ would be okay if the bar went under - he knew Bobby’d give him a place at the garage, no problem - but how would Dad pay his debts? Mechanic paycheck wasn’t going to cover that. 

Lord knew there was no one else around to help out.

He could hear the cautious hopefulness in Ellen’s voice. “I don’t suppose you would... with, ah, Anna -”

“No,” Dean snapped. “Don’t even go there.”

“Dean -”

“She’s not even legal, Ellen!” He pushed away from the table and started pacing, angry.

“She’s close,” Ellen argued. “And that money -”

“I’m not taking money from a kid who’s got a crush.”

“Could be more than a crush,” Ellen said, a sharp look in her eye, and Dean turned his back on her.

He should have shut this whole Anna thing down months ago. Yes, she was a lot nicer to have around than Zach, and he wasn’t going to turn away any paying customers, and okay, she was super hot - but super hot was relative when she was practically freaking jailbait. Dean wasn’t a monster. 

The whole thing had gotten _so_ out of hand. It was his fault for getting drunk behind the bar, even once, even just a little. She’d cornered him in the back hallway, and they’d started kissing - barely even necking, hands on the waist at all times - before he’d remembered himself and sent her home. But it’d been enough, apparently. The way she _looked_ at him now - and crap, after tonight, she probably figured he’d _met the family_...

He was such an idiot.

“No way,” he told Ellen. “Eventually she’s gonna get over it, and I’m not gonna have her already’ve sunk her cash into this place when she does.”

“You want to take Zach’s money instead?” Ellen asked, arching an eyebrow.

Dean shuddered. “Don’t even joke. That old queen is way too creepy.”

“So how do you plan to pay the bills?” Ellen asked. 

“I don’t know.” The tightness in his chest was becoming familiar, and Ellen was starting to look at him like she could see it. But keeping her from worrying was just another turn of the bolt.

“Dean,” she asked, voice not quite as business-like anymore, “When’s the last time you called -”

“Goodnight, Ellen,” He said with finality, and turned to the stairs that lead up to his tiny apartment over the bar.

It had been John’s before Dean took over, and in a lot of ways it still was - he hadn’t taken much with him from Cicero. He’d left most of John’s stuff where it had been, jackets in the closet, newspaper clippings on the tables, dirty mugs in the sink. The stack of bottles in the corner he’d taken out to recycling the day he’d moved in. 

The room had probably begun life as some kind of extra storage for the bar, so it wasn’t exactly homey, but it was convenient. 

Dad was probably bitching up a storm, being “forced” to sleep on Bobby’s couch while Ellen and Dean tried to wrestle the bar into shape, but Dean knew he was enjoying it. Bobby’s nagging, probably not so much.

Through his tiny window, Dean could watch the night’s refugees from his and other bars wander the streets, searching for home or each other or the next diversion. His day would start again in less than eight hours.

He was so screwed.

*

The sun was still bright through the windows the next day when Castiel appeared outside the bar.

He gave a tentative wave as Dean frowned at him from above the tables he was wiping down, and pointed at the lock on the door. Confused, Dean unlocked it and held it open just wide enough to squint out at him.

“Hey,” he said, trying for a grin but probably coming up empty. “You that impatient for another burger?”

“Actually, I came to speak to you,” Castiel said, face sober like the shots and the darts had never happened. “Would you like to take a walk?”

Dean hesitated. The Roadhouse was on a decent block, actually - too close to the wrong part of town to be the kinda place where people with real money (like Cas) went, but decent. And it was facing a nice park, and the sun was shining down hot for it being barely April, and Dean hadn’t felt it on his face in... he couldn’t even remember.

But something about the bottomlessness of Castiel’s eyes made him uneasy. If anyone else had come around like this, after acting the way Cas had last night, Dean would have thought he was getting hit on, but he knew that wasn’t what was happening. Did he really care that much about his sister being in the company of drunks?

Never one to resist a mystery, Dean said, “Sure,” and retreated back in the bar just long enough to grab his keys and wallet before locking the door behind him and starting down the street with Cas.

He didn’t keep him in suspense for long. “You can’t have gotten much sleep.”

 _What._ “What?”

“You must have worked ‘til 2 or 3 last night, and here you are, already prepping for another day,” he explained.

Uncomfortable with the idea of Castiel thinking that closely about his schedule, Dean shrugged and said, “Running a bar’s not easy.”

“Especially in your circumstances.”

Dean turned to stare at him, scowling. “My what?”

“Anna told me the bar is struggling,” Cas said calmly. “And has been for some time.” 

Anger flashed through him, searing the inside of his skin. “Did she? Well, that’s...” he paused, swallowing down cruder words. “Great.” 

“You’re nervous.” 

“I’m wondering why you’re here, Castiel,” Dean said shortly.

“Because I can help you.”

There had to be a cap on the number of times Dean could have to ask what the hell Castiel was saying. “You can what?”

“I can help you,” Castiel said. “With the bar. I know you’re aware of my family, of who we are. I can assist with your financial burdens.”

“And why would you do that?” Dean asked.

Castiel stopped walking as they passed under a large tree, the dappled light obscuring some of the detail of his face. “Because there’s something you can do for me.”

Dean’s heart sped up. _Was_ Castiel hitting on him, albeit in his creepy, zombie millionaire way? He felt an unaccountable sensation of... disappointment. He had seemed different. “And what’s that?”

“Stop,” Castiel said simply.

“Stop what?”

“Stop seeing Anna. Stop speaking to her, stop inviting her to the bar, and certainly stop...” Cas paused here, seemingly not for effect but more as if he had never had to use these words before: “Stop giving her the impression that she can win your affections with her trust fund.”

 

_Win your affections?_

_With her trust fund._

_... win your affections. WITH her trust fund._

Dean was frozen from the inside out, his brain parsing Castiel’s words sluggishly. The Ravens actually thought Anna was serious about Dean? Serious enough to send someone to - hang on a minute, _win your affections?_ Did they think Dean was some kind of - con artist? Gold-digger? Whore?

Castiel had just offered to pay him to leave, so he was guessing the answer was yes.

Rage filled him slowly, like a thick, noxious smoke snaking from the soles of his feet to the corners of his eyes. His fists itched as he watched Castiel patiently wait for an answer, aching to pound that polite interest off his face. He wanted to make him a stain on the pavement. He wanted to tell him that he wouldn’t have _affections_ for his sister if he paid him to do _that_ , and that their entire goddamn family could go to hell. He opened his mouth to say all of that and more, much more colorfully, as a prelude to the stain-making.

Until it occurred to him that a good old-fashioned beating was far too pleasant a punishment for someone like Castiel.

He forced his face into smoothness, raised his eyebrows, and asked, “And how much would it cost you for me to... stop?”

“I’ll give you ten thousand dollars.”

Dean barely heard the amount; he barked with laughter. “You know, you were right, Cas: I am _aware_ of your family, of what you’re worth, what Anna’s worth.” He grinned predatorily. “Try again.”

Castiel frowned, the first hint of a chill appearing in his eyes. “I didn’t come here to bargain with you.”

“Seems to me that’s exactly what you did,” Dean said. “Except you severely underrated how in love with me your sister is.”

Something cracked in Castiel’s face, the edges sharp like glass. “I am having a hard time imagining why,” he ground out.

“But you’re here,” Dean said. “Your family must be pretty worried about Anna running away with a low-life like me.”

“I am worried about my sister throwing her life away on a man who is using her for her _money_ ,” Castiel spat, taking a step closer to stare up into Dean’s face.

Dean’s smile felt like it was carved from stone. “Then show me how much.”

It was like he could taste Castiel’s glare, sour and curdling in Dean’s gut. “Anna does not have any assets at present, beyond the limited amount we give her as living money. Her car and apartment are both owned by the family. She is useless to you until her birthday.”

“Her birthday’s coming up,” Dean said, biting down _useless to_ you. “About two months, isn’t it? I can afford to wait.”

A muscle in Castiel’s jaw ticked. “Twenty thousand.”

Another laugh tore out of Dean’s throat. “You’re asking me to turn away an entire Raven bankroll for only a fraction in return?” Dean said. “Who knows, maybe one day I’ll put a ring on her finger.” Castiel’s eye twitched. “Then I won’t just have the cash, I’ll be a part of one of the richest, most powerful families in the country. That’s a lot of temptation.”

“That,” Castiel said intently, “will never happen.”

Dean loomed over him as best he could, with Castiel being all... also tall. “And what are you going to do about it?” 

Cas narrowed his eyes and cocked his head to the side. “Anna is only twenty. You must be at least thirty.”

“Twenty eight,” Dean said reflexively.

“You’re her first crush,” Cas said. “It won’t last. You know it won’t.”

“It’ll last for another two months,” Dean purred. “I’ll make _real_ sure of that.”

“I’ll tell her,” Castiel countered. “I’ll tell her you’re using her for her money.”

“And that you offered me even more money to leave her alone?”

Castiel grimaced, but said, “And that you bargained with me instead of refusing.”

Dean scoffed. “Try it, Cas. She’s real close with your family, right? Real trusting?” He took sick pleasure in watching Castiel’s face fall as the implications of that particular move spun out in his head. “Ohhh, right. She hates you, she’s looking for any excuse to get out.” Dean took a leisurely step forward, goading Cas. “Go ahead. Give her one.” 

Cas looked ready to explode. “And what price do you put on yourself?”

“I don’t know, Cas,” Dean mused. “But I do know it’ll go up as Anna’s birthday approaches.”

Cas seemed struck into silence at that, and Dean knew it should be his cue to walk away, but he just couldn’t help twisting the knife. “What am I going to do with Anna’s money once the bar is up and running?” He asked rhetorically. “We can build a big house, of course - with a pool, and a guest house, and ooh, we could have monster trucks out back instead of tennis. She’d love that.” Veins Dean didn’t even realize existed were twitching in Castiel’s forehead. “I could start my own beer company. Or a pie company. Ooh, or a _theme park_. I’ll call it Deanland.”

“Trying to drive up the price?” Castiel asked through his teeth. “It won’t work.”

Dean walked all the way back up to Cas so he could lean over him as he said lowly, “A hundred thousand dollars.”

Cas’s eyes went wide and dark, then narrowed. “Deal.”

Dean let the silence drag out a minute, then leaned back, laughing hysterically. “I’m just fucking with you, Cas. There’s no amount of money you could pay me to give up your sister. She’s mine, and there’s nothing you or your family can do to stop it.”

He’d already started walking back to the bar, content with his parting shot, but he could just make out over the wind through the trees Castiel’s low, “We’ll see.”


	2. Chapter 2

_Four Days Earlier_

Castiel arrived at his stepmother’s summons exactly on time, for which she showed her appreciation by greeting him with: “We have a problem. It’s Anna.”

He ignored both of the chairs in front of her desk, choosing instead to stand by the window. “What’s wrong?”

Naomi reclined in her chair, assessing him carefully. “She wants to invest in a bar.”

Castiel frowned - his most recent interaction with Anna had been her emailing him a series of pictures of something called _flower crowns_. “Really?”

“Yes.”

“Since when has Anna been interested in finance?”

“Since she met the bar’s owner,” Naomi said ominously. “He is a former car mechanic, has a GED, and is apparently... I think the word is - hunky?”

Castiel grimaced. “Ah.”

“The bar - the Roadhouse -” her mouth stumbled over the syllables like she was trying not to touch them, “is falling apart. It’s in the worst area of town, a magnet for drug dealers and bikers - a den of iniquity.”

Castiel chose to ignore Naomi’s colorful language. “How did Anna end up there?”

“Oh, you know how she is lately. Headstrong, defiant - that _garish_ red hair...” she trailed off, disgusted. Castiel privately thought that Naomi’s hair color was less garish but no more authentic. “And in this moment of... vulnerability, this _leech_ has attached himself to her,” she finished, furious.

“They’re involved?”

Naomi waved a hand dismissively. “She says no, but it’s obvious something’s going on. I’ve seen this before - first it’s his bar, then who knows what - she’s buying him drugs, supporting his _band_ -”

“He has a band?”

“Does it matter?! Castiel, you’ve got to put a stop to this,” Naomi pleaded, fists pressing into her leather desk pad.

“I think you’re blowing this out of proportion,” Castiel said. “She’s twenty. She’ll go through plenty of leather-jacketed drifters before she’s through.”

Naomi sneered. “You would know.”

“I appreciate our talks,” Castiel replied, inclining his head and turning for the door.

“Castiel, wait,” she said, and he paused without turning. “Even if you’re right, we don’t have time to hope her affections wane.” And - there it was.

“June,” He said slowly, turning. “She’ll come into ownership of her trust.”

“He has to know,” Naomi said. “This bartender. He’s preying on her, Castiel, and she’s letting him, because -”

She broke off, unwilling or unsure of how to put Anna’s grievances with the family into words. Castiel didn’t help her.

“Why don’t you just cut her off?” 

“You know I can’t,” Naomi said, scowling, and he did know, he just liked to see her admit her helplessness. “Anna’s the best, Castiel,” Naomi said softly, big eyes pleading now. “The best of us, maybe since Michael. The smartest, the most potential -”

“Spoiled, if you ask me.”

Naomi raised her eyebrows. “You’re just upset she used to beat you at chess. When she was _ten_.”

“As I said,” He said, inclining his head as a tiny smile tugged at his mouth, “spoiled.”

“You have to talk to her,” Naomi said, the memory sliding off her face. “We can’t let her be taken advantage of by this - this - _parasite_.” She leaned forward, bracing her palms on her desk. “Castiel, you’ve... you’ve been through some of what Anna’s going through. You understand.”

Castiel’s position by the window was strategic: taking in the garden view was an excellent excuse not to have to look at Naomi’s face. “She’ll listen to you,” she was saying. 

“Because younger sisters always listen to their older brothers in matters of romance,” Castiel quipped.

“She’s not listening to me,” Naomi said. “Please, Castiel. This could ruin her entire life.”

“You don’t need to convince me,” Castiel said, heading for the door. “Send me the details and I’ll take care of it.” 

“Be careful, Castiel,” he heard behind him. “This man is charming, manipulative. The last thing I need is _you_ getting caught in his spell.”

Castiel cocked an unimpressed eyebrow at her by way of reply, and shut the door behind him.

*

Ellen jumped when the door to the back room smacked against the wall as Dean stormed in. “What the hell - ?”

“Son of a bitch,” Dean fumed. “I’m gonna - gonna -”

“I take it this has something to do with Raven the elder?” She asked. “Crowley said he saw him come by.”

“That _asshole_. Scheming, two-faced -”

“Words, sweetheart,” she said, stopping him with a hand on his shoulder. “What'd he do?”

“ _Affections_ ,” Dean muttered. “I'll show him _affections_. I'll make him sorry he and his sister and their whole damn family ever heard the _name_ Dean Winchester.”

“Anna?” Ellen asked, frowning. “What’d Anna do?”

“She - nothing.” Dean deflated slightly. He sat in a chair, feeling slightly sick at the thought of telling Ellen what Cas had thought of him. But: “Castiel was here to offer me ten thousand dollars never to talk to Anna again.”

Ellen’s jaw dropped, and she guppied for a moment. “I - I - ” Her face was all warm concern. “What did you say?”

“I don't really remember,” he confessed. “I think I told him to go fuck himself, and something about building a theme park called Deanland with Anna's money.”

Ellen’s eyebrows hit her hairline. “You what?”

“That piece of shit,” Dean seethed, ignoring her. “Said I was _seducing_ Anna, that I was _using_ her for her money.”

“That's ridiculous,” Ellen said. “How would they have gotten that idea?”

“I don't know!” He shouted. “Sure, she comes around here a lot, and yeah she's got a crush, but I'd never do anything! She's -” he paused, mood softening momentarily. “She’s sweet. Good. And almost half my age!”

“Did you tell Cas that?”

“No.” He gave a tight grin. “I told him ten k was chump change compared to the Raven family vault.”

“You _what?_ ”

“Yup. So he offered me double.”

Ellen swayed a bit, and grabbed the back of the chair behind her. “Twenty thousand dollars? That... that'd clear a lot of our debts.”

“I laughed in his face,” Dean told her. “Told him I'd marry Anna and be on her dime forever.”

Ellen frowned. “But you just said -”

“Obviously I'm not gonna do it,” Dean explained, waving a hand, “but he has to pay. That fucker. He was willing to offer me a _hundred thousand dollars_ just to disappear.”

“A hun -!” Ellen’s eyes bugged, and she sank into the chair she’d been gripping. “I need a drink.”

“Obviously a bartender's not _good enough_ for little princess Raven,” Dean continued, but stopped at a look from Ellen. “What?”

“Oh, nothing,” she muttered, staring into the flask she’d produced from nowhere. “I've just never heard _that_ before.”

Dean flushed. “I - it's different.”

“So... let me get this straight,” she said after a healthy swig. “You wouldn't take Castiel's money, and you're not taking Anna's money, or Zach's.”

Dean nodded. “Right.”

“So what are we going to do about the bar?”

Dean gaped. “You think I should’ve taken Raven's blood money?”

“It's not blood money, it's -”

“You want me to whore myself out for Castiel,” he said flatly.

“Why don't you take his money, and then tell Anna about it?” Ellen reasoned. “I bet the two of you would have a laugh. What's he gonna do? Sue for breach of the world’s dumbest contract?”

“No,” Dean said, shaking his head violently. “He has to pay. Worse than just losing his money - he needs to _suffer._ ”

Ellen was looking at him again, the same look she’d had on her face when he’d crashed his bike when he was seven and skinned his knee. He scowled and took the stairs to his room two at a time, the phone in his hand and ringing before he knew it. 

A woman answered. “Sam’s phone, what d’you want?” 

The familiar, grating voice was like a bucket of cold water over his head. He threw the phone across the room.

A few deep breaths and some strategic planning later, he coaxed the phone out of its broken case and dialed another number.

“Hey Anna,” he said, making sure she could hear the smile on his face. “What’re you up to?”

*

Castiel sat at his desk and replayed his conversation with Dean over and over again, growing more furious with himself by the second.

_A hundred thousand dollars._ He’d made the offer - he’d actually been willing to do it in that moment - because Dean had made him see red. 

How the hell had their conversation gone so off the rails? 

He had been expecting Dean to protest, play dumb, perhaps be somewhat insulted or coy. It would have tracked with the Dean he’d met last night - the flirt, the charmer, the consummate host: coaxing Castiel to talk about his family, goading him into ordering more shots, smiling that intoxicating smile, crowding around him to _play darts_ \- please. Castiel may have been telling the truth about not knowing the game, but he wasn’t an idiot. Not to mention his other target, that poor older man he’d gone running to any time he’d spent too long at Castiel’s side, expertly balancing his lures so that none of the fish ever bolted. Who knew how many other _offers_ he was entertaining? Dean was - he was the serpent offering Eve the apple. No, Dean _was_ the apple - juicy and tempting. 

Castiel ground his teeth.

His flustered reaction when he’d discovered Castiel’s relationship to Anna was the final proof of his duplicity - he’d tried to cover with that older-brother shtick, _we’ll take care of her, sir, don’t worry_. So yes, Castiel had been expecting some pushback today, some denial. But not -

When he had made that final, ludicrous offer - he knew in his bones that Dean’s considering pause had just been theater. He hadn’t considered actually taking the money for a second. It was almost as if he’d been intent on refusing Castiel the entire time.

Which made no sense. Though he knew Dean was interested in his sister’s money, he hadn’t thought _so_ poorly of him after their first meeting - quite the opposite, in fact. Charmer he may have been, but he’d also seemed honest, down to earth, and genuinely struggling to keep his bar open. Castiel sympathized with that, he did. It’s why he’d been willing to make the original offer.

Dean had seemed desperate, but not like a social climber. Not someone willing to - a _theme park?_

He remembered the flash in Dean’s eyes when he had made his first offer. He had looked almost angry - furious, even. But he couldn’t have been. He was simply much more manipulative, with much grander goals, than Castiel had given him credit for. 

Castiel was not used to being defied, especially not by people outside of his family. He wasn’t an elitist, but his family tended to be... strong-willed in a way that set them apart from others. Normal people were, in his experience, either cowed or envious of his them, and eager to please for either reason. 

Dean was not. Perhaps that’s what Anna liked about him. Still, it wouldn’t do.

The phone ringing startled him from his dreary contemplations, and he answered before looking at the name on the screen.

“Cas!” Anna screamed. “You’ll never believe it, guess what, guess what?”

“Anna?” He asked, confused. “What?”

“It’s Dean!” His heart stopped, but before he could even grasp for an explanation, she said, “He finally asked me out, on a real date!”

“He -” Castiel paused. “What?”

“Oh, I know what I said, about wanting to take things slow,” Anna said in a rush. “But I’ve been telling him for _weeks_ about tonight’s charity auction, and he finally said he’d go!”

“To - to tonight’s - with -” Castiel sputtered.

“I know, everyone’s going to be there, that’s why I wanted to call you,” Anna said. “I need your help with Naomi - smooth things over with her, please? I know she won’t make a scene in public, but this is my chance to show her that Dean - how amazing he is!”

“Right,” Castiel agreed shakily. There were another sixty seconds of squeaking and general enthusiasm about Dean, dazedly echoed by Cas, before she hung up.

He was even more baffled than before. Dean’s first move should have been telling Anna everything that had happened - he clearly knew she was on thin ice with the family, and this would have turned her against Cas along with the rest of them, further strengthening Dean’s hold. Instead he was... going to a gala?

Castiel began to feel reluctantly interested in the inner workings of Dean Winchester’s mind.

*

“Trashy women?” Crowley asked, eyebrows arched.

“Yeah, you know any?” Dean said, rummaging around through the stock room for their cheapest booze.

“Do I know any,” Crowley chided him. “Why the devil would you ask?”

“I’m going to a party tonight,” Dean said, having found something called LunAzul that looked promising. “You’re coming with, and I need you to bring a date.”

“A trashy date?”

“The trashiest,” Dean said. “Someone with no manners, or class, preferably something growing on her face - mustache, cold sore, fetal twin, the details are up to you.”

“I’m at your disposal,” Crowley said with a miniature bow, “but may I ask why?”

“Apparently Anna’s family is terrified at the thought of her dating me,” Dean said slowly, with a humorless grin. “I want to make them... more terrified.”

“But you’re not dating Anna,” Crowley said, frowning.

“I am now,” Dean said, and experimented with dribbling a little of the tequila in his palm and then splashing it against his neck. Crowley grinned.

“Trashy date,” he said. “On it.”

He passed Ellen on his way out, who gaped at Dean once she got a good look at him. “What are you wearing?!”

“Not enough,” Dean mused, though he’d been pretty pleased to find the beer-stained wifebeater at the bottom of his laundry. “Do you have anything with the confederate flag on it?”

“With the - why on _earth_ would I have anything with the confederate flag on it?” Ellen growled.

“No reason,” Dean sighed. “Where do you think I can find some really gross temporary tattoos?”

“Dean.” She grabbed him by the shoulders. “What’s going on?”

“I’m meeting the family,” Dean said, and let an expressive handwave explain the rest.

“Oh my god,” Ellen moaned. “What is _wrong_ with you, boy?”

“Nothing,” Dean grinned. “Hey, do you think I have enough stubble to shave into a chin-strap?”

“I don’t know,” Ellen asked. “What’s _Anna_ going to think of your chin-strap?” 

Dean shrugged. “If she really loves me, she won’t care.”

“If she really loves you,” Ellen said shrewdly, “you’re breaking her heart for nothing.”

Dean scowled. “It’s only for a few weeks. And it’s only because her brother’s an unimaginable dick.”

“Seems to me she came here to escape her family, Dean.”

“Yeah, well, her family found her.” Dean sat down to drag on a boot. “I’m her first crush. She’ll bounce back.”

Ellen leaned against the wall and surveyed him critically. “You could have just told her what her brother said. Then you could have taken him on together.”

“Uh huh,” Dean said, and focused on slipping on the other boot.

Ellen knew enough to recognize when she’d gotten the most she was going to get out of him, and wandered away with a sigh that sounded suspiciously like _id’jit_. Dean honestly had nothing to say - it had occurred to him, of course, but the idea had never gone much further than idle, entertaining speculation. It was something in the way Anna had looked at Cas when he’d come in the bar last night, so thrilled, almost worshipful. Happy. 

It wasn’t smart, but Dean had a stubborn sense of loyalty to older brothers.

*

Naomi’s voice floated up from Castiel’s phone as an indignant squawk. “How can there be nothing to report yet?”

Castiel sighed into his palm. “I went to the bar, assessed Winchester and the state of Anna's relationship with him, and returned this morning with a... preliminary offer.”

There was a rushing sound, like the wind, or a car, or most likely someone Naomi had knocked over as she swooped down the street between meetings. “A _preliminary_ offer?”

“It - it did not go as well as I had hoped.”

Naomi’s voice was thunderous. “What does that mean?”

“It's worse than we thought,” Castiel said. “He won’t take a buy-off - he's determined to marry Anna and become a permanent part of the family.”

“You mean he wants to bleed us for a lifetime,” Naomi said grimly.

“Don't worry,” Castiel said. “I'm taking care of it.”

“I don't know about this, Castiel. Maybe I should step in.”

“I don't think that would help,” he said delicately.

“Tell me about him,” she said crisply. “Is he crude? Uneducated?”

Castiel stared up at his office ceiling, remembering how Dean’s smile had crinkled the freckled skin around his eyes. “He's no academic, but he’s not vulgar or off-putting. Quite handsome.”

“Of course,” Naomi said dismissively. “Why else would Anna have so completely lost her senses?”

“It's not just that,” Castiel said. “He's... funny. Self-deprecating. Real.”

“What the - Castiel, don't tell me _you_ -”

“Of course not,” Castiel scowled at the phone. “That's just how he _seems_ \- what he's using to lure Anna in. When I confronted him about it, he showed his true colors.” He paused, grimacing. “You’ll get a chance to see for yourself tonight.”

“Tonight? What do you mean?”

“Anna is bringing him to the charity gala.”

“ _Castiel,_ ” she intoned. “You - we simply must - he can’t be allowed to -”

“He won’t,” Castiel pledged. “Come to the event tonight, act as normal as possible. We have to show him we won’t be blackmailed.”

“If we can’t buy him off, what are you going to do?”

Castiel’s eyes were on the phone, but he didn’t see it. “Destroy him.”

“What does that mean?” Naomi asked tartly. He hung up, and then spent several long minutes thinking of exactly what _destroying_ Dean would entail, before his impotent rage was interrupted by the buzz of his intercom. “A Mr. Adler here to see you?”

Castiel frowned, but told Rachel to show him in. Mr. Adler turned out to be the infamous Zachariah from the bar the night before. Castiel raised his eyebrows.

“Mr. Adler,” he said, rising from his seat. “What a surprise.”

“Please, call me Zachariah,” the man said with a nauseating smile. He settled himself in one of the chairs in front of Castiel’s desk. “I’m actually surprised we hadn’t met yet, Adler has several contracts with Raven Enterprises.”

“Oh? Is that why you’re here?”

“No,” Zach said, his smile thickening. “It’s about last night.”

“Uh, yes,” Castiel stuttered. “About the, ah, dart -”

“Oh, no need to worry about that, no harm done,” Zach said, waving a simpering hand. “I’ll admit, I had been expecting you to stop by the Roadhouse earlier.”

“You had?”

“Anna’s been haunting the place for months,” Zachariah said. “I was expecting the cavalry to come save her from herself much sooner.”

Castiel tilted his head slightly and let the silence linger just long enough for Zachariah to shift uncomfortably in his seat. “Save her?”

“The girl can’t even be of age yet,” Zachariah said. “And that area of town, the type of people... it’s not the proper environment for a young lady of Anna’s stature.”

“You seem to spend plenty of time there,” Castiel said.

Zachariah grinned. “What a grown man chooses to do with his time is very different from how an impressionable young girl spends hers, isn’t it?”

“Why are you here, Mr. Adler?” Castiel asked impatiently.

“To tell you how glad I am that you’ve seen the kind of environment the Roadhouse is,” Zachariah said. “And that you now know it’s not a fit place for the young Miss Raven.”

If Castiel was good enough to conceal the depth of his panic from Naomi, Adler posed no threat to his composure - no need to show his cards before he knew the full extent of his involvement. “It seems like you know it’s no place for my sister,” Castiel said. “All I know is that they cook a mean burger.”

“Come now, Cas, no need to be coy,” Zach chuckled. “Why else would you have visited? Anna’s... _interest_ in Dean Winchester is worrying, I don’t blame you for wanting to nip it in the bud.”

“I can see why Anna would be worrying to you, given your own interest in Mr. Winchester,” Castiel said softly.

Zachariah’s smile stayed fixed in place. “Then it seems removing Anna from the scene would be of mutual benefit to both of us.”

“And if I hadn’t stopped by the bar,” Castiel asked, letting the hostility in his gaze pin Zachariah in place, “what would you have done to _remove_ Anna in that case?”

“Why dwell on a hypothetical?” Zachariah said blandly. “You’re aware of the situation now, and I trust you’re doing everything in your power to rectify it. Believe me, you do not want Anna throwing herself away on a money pit like the Roadhouse.”

“But you’re willing to throw yourself onto it?”

“I know what I’ll be getting,” Zachariah said. “Once Dean comes around, ours will be a clear-headed business arrangement. Anna... she’s being guided by her heart. Dean will break it.”

“I’m not sure he isn’t sincere about her,” Castiel lied, watching Zach’s reaction carefully.

“Please,” Zachariah snorted. “They’re desperate. Dean... he’s gorgeous, but he’s not exactly a numbers man. And that aunt of his - sweet, bakes a great pie, but, well. It’s clear the task of running a business is a bit beyond her.” 

“I’m surprised you know so much about their financial situation.”

“Of course,” Zachariah said. “I hold several of their debts.”

“Really?”

“Oh, yes. The previous owner, John Winchester, was even sloppier than Dean and Ellen,” Zachariah explained casually. “He took out loans from some very shady characters. Once Dean took over I sniffed around a bit, and was able to transfer them into my own portfolio, where they’re more... secure.”

“I see.” Castiel leaned forward on his elbows, regarding Zachariah frankly. “If you hold the debts on the Roadhouse, why don’t you just use them to... _get_ Dean?”

“Oh no, no no no,” Zachariah fawned, “he has to _want_ it. Consent, and all that.”

Castiel felt sick to his stomach. “So you don’t want to pressure him, you want me to do it for you?”

Zachariah grinned smugly. “I simply want you to take care of your sister.”

Castiel glanced down at his phone, thumbing through his calendar for the day. “Thank you for coming by, Zachariah.”

“Oh, thank you, Cas,” Zachariah said, standing. “I look forward to working with you.”  
Castiel said nothing as he let himself out of the office, but sighed once he was gone.

This grew more complicated by the hour.

*

The address Anna gave him turned out to be an aged brownstone in a part of town Dean had never been to before, and for good reason - the lawns were perfectly trimmed, the air fragrant with the scent of flowers, and the people milling on the lawn decked out in clothes that probably cost more than the Roadhouse brought in in a month.

Crowley himself had an uncanny ability to fit in anywhere, but the woman at his side, a petite blonde, looked singularly out of place. She was actually a _very_ recent blonde, Dean discovered as he drew nearer, her harshly bleached curls drawing not a few curious glances from the other gala-goers.

“Crowley,” he greeted him. “Who is this lovely creature?”

“Meg, Dean, Dean, Meg,” Crowley drawled. 

“Hiya,” Meg said, crimson lips smacking on gum. Dean grinned as he shook her hand.

“A pleasure.”

“Have I come through or what?” Crowley asked.

“Always,” Dean told him. 

The gala was being hosted in the brownstone’s courtyard, twinkling lights strung up between the trees illuminating the small tables and occasional pedestal on which a painting or sculpture was displayed. It was all modern art, the kind that looked like someone had tripped over a paint can and then demanded a million bucks for the splotch on canvas. Still, the champagne tasted expensive and the bacon-wrapped scallops were delicious. Dean had three in his mouth when Anna found him.

“Dean!” She squealed, giving him an automatic kiss on the cheek, before she pulled back and her expression dimmed somewhat.

“Hey sweetheart,” he grinned after swallowing. “Everything okay?”

Her face was frozen in a tiny O of surprise as she took in his outfit. Ellen had eventually peeled the wifebeater off him and helped find a suit in her closet that she _swore_ wasn’t one of Bobby’s from decades ago, but Dean wasn’t too sure - it was burgundy corduroy, flattened and frayed with age, just a hint too small, so that it bunched and bulged out along the shoulders and waist. He’d left his shiny black dress shirt unbuttoned just enough for a sliver of his tattoo to peek through, and had managed to splash a bit more tequila on himself after Ellen had scrubbed the original dose off.

“You... look ... wow!” Anna told him, a taut smile on her face.

“Yeah, sorry about this, I knew I needed to dress up, but...” he let the sentence trail off, which had the expected result of turning her worry into warm, slightly pitying understanding.

“It’s fine!” she said, leaning up to give him a tentative kiss on the lips. “You know you always look great.”

_Sweet kid._ She looked beautiful in a simple black dress, with her hair down and glinting in the soft light. Dean gestured behind him: “You know Crowley, and this is his friend Meg.”

“Of course!” Anna said, smiling. “Thanks so much for coming.” (She’d been a total pushover when Dean had expressed some nervousness about going to his first Raven family function alone.)

They only enjoyed a few minutes of Anna’s blissfully nonjudgmental company before the tide of the party brought them toward a group that even the other party-goers were hovering around like royalty. Dean recognized one particular set of shoulders even from behind, and grimaced.

“Cas!” Anna tapped him on the back and engulfed him in a hug before he had fully turned around, depriving Dean of the opportunity to get a good look at his face when he first saw the Roadhouse crew. By the time Anna had pulled back he wore a mask of frosty indifference. 

But the woman to Castiel’s right made up for everything that Cas had lacked - when she turned around, her face immediately pulled into an immensely satisfying horrified pinch. 

“Naomi,” Anna was saying, “this is my date, Dean Winchester, and these are his friends, Crowley and - Meg?”

“That’s me,” Meg said, thrusting her hand forward. Her nails were painted highlighter yellow. “Hey there.”

Naomi looked like she wasn’t sure if she should scream or break her champagne flute on a table and impale Meg with it. Dean stepped in.

“Mrs. Raven, it’s such a pleasure to meet you,” he said, grabbing her hand and shaking it enthusiastically. “Anna’s told me so much about you, about your whole family, and I think this charity thing y’all are doing is awesome.” He gestured around to the paintings, letting his arms flail a bit too much. “I mean, I’m not one for high art or anything, but these all look real good. I do have an art poster in my room - I live above the bar I work at, the Roadhouse? I’m sure Anna’s told you all about it - it’s black and white, and has two ladies kissing, but not hardcore or nothing. It’s real tasteful.”

A snorting sound stole his attention from Naomi’s rapidly darkening face, and he started a bit to see Castiel attempting to hide his face behind a cocktail napkin as his shoulders shook.

Before he could focus on that, Naomi reached out a hand to rest gently on his shoulder, and said with a sickening smile, “Dean. So lovely to meet you at last - shall we take a stroll around the party, get to know each other better?”

He grinned widely. “Yes, please! Anna?”

“Of course,” she said, beaming. “Have fun!”

Castiel turned to Anna as soon as they were out of earshot, Growlson or whatever his name was and his horrendous date having wandered off lord knows where. “If this is your attempt to impress Naomi...” he muttered.

“Shut up,” she whispered back. “Can’t you see he’s nervous? He’s not used to these types of parties.”

“So you decided to leave him alone with Naomi?”

“Once he calms down and acts more like himself she’ll see what I see,” Anna said confidently. “I just know it.”

Naomi returned twenty minutes later, after Anna had gone to chat with one of the artists, looking ashen. “That bad?” Castiel asked her.

“We _must_ pay him,” Naomi hissed. “Anything it takes!”

“No,” Castiel scowled. “You’ve seen for yourself; we can’t let him win.”

Naomi shuddered. “I can’t believe you. You said he wasn’t that bad!”

“He wasn’t,” Castiel said bluntly. “Yesterday. Today it seems he’s trying to drive up the price.”

“Anything,” Naomi pledged. “Anything, Castiel, just get him away from Anna. He was going on about -” she winced. “ _Country music._ ”

The thought of Naomi being forced to endure that conversation was momentarily amusing again, but Castiel ruthlessly quashed the thought.

*

Dinner was served at a series of long tables each decorated with a candle centerpiece that looked like its own modern art. With Crowley and Meg MIA (though he hoped, wherever they were, still causing a scene), Dean found himself seated at the very end of one table with Anna to his right, Naomi across from her, and Castiel across from him.

He was, frankly, exhausted. Being a nuisance to everyone around him on a constant basis was draining - but it had been worth it to see Naomi struggle to keep calm as he went on and on about the glory days of Skynyrd. 

When the waiters had dropped off their salads, Anna nudged Dean playfully and told Naomi, “I usually order salads at the Roadhouse, and Dean always teases me.”

“And why is that?” Naomi asked frostily.

“Because man - and woman - were meant to eat the flesh of lesser beasts,” Dean said, biting into a tomato with a grimace. “Not this... rabbit food.”

“I see,” Naomi said, gently spearing some lettuce.

“Cas here knows what I’m talking about,” Dean said with an exaggerated wink.

Naomi turned to him, raising an eyebrow. “Dean’s burgers are delicious,” Castiel said calmly.

Anna beamed. “I’m going to get a glass of wine, anyone else want anything?”

“Another beer?” Dean asked, though he had thrown the last two in nearby ficuses.

“Sure,” she said, leaving her napkin in her seat as she wound her way to the bar.

“I didn’t realize you were a fan of bar food,” Naomi told Castiel, glaring at her salad.

“It’s good when you have a craving,” Castiel said, staring at Dean. “Not on a regular basis, of course.”

“Mm, you don’t know what you’re missing,” Dean replied. “Pie for breakfast? Heaven on earth.”

“Excuse me,” Naomi said stiffly. “I feel suddenly unwell.” She rose from the table and headed indoors, leaving Dean and Cas alone at the table.

“Nice suit,” Castiel said lightly.

“Thanks,” Dean said, chewing with his mouth open. “It’s a little run-down - maybe I’ll ask Anna for some cash to get it mended.”

Castiel’s eyes flashed. “I can see why you’re going broke - you spilled most of the bar’s inventory on yourself.”

Dean opened his mouth to reply, but Anna sat down next to him with drinks in hand, and he hastily shut it. Castiel’s eyes travelled between him and Anna, calculating.

“So Cas,” Anna said, taking a sip of her wine. “Your meeting’s coming up - next Friday, right?”

Castiel frowned at Dean before returning his gaze to Anna and saying only, “Yes.”

“Nervous?” She asked, smiling.

“Meeting?” Dean asked.

“Oh!” Anna said, seemingly realizing he was out of the loop. “Cas is trying to open a low-cost health clinic downtown, and he has a meeting about it on Friday with an angel investor. It’s so exciting!”

“Hmm,” Dean said. “That’s, uh... real charitable of you, Cas.”

“It’ll be charitable of the investors,” Castiel said, forking up the last few bites of his salad. 

“Investors?” Naomi asked, sitting back down at the table.

“For, um, the company,” Anna said hastily.

Naomi looked faintly amused. “I didn’t realize you were interested in Raven Enterprises, Anna.”

Anna blushed slightly. “Well I was just asking Castiel about work, so...”

“That’s wonderful,” Naomi said. “Maybe we should talk about a summer internship, for after graduation.”

“Actually...” Anna said, looking more nervous by the second. “Naomi, do you think we could -” she glanced at Dean, then back again. “Could we talk for a moment? Privately?”

“Of course,” Naomi said smoothly, and they both rose from the table.

“Health clinic, huh?” Dean asked once they were gone. “You do realize the people who go to those are, y’know. Poor.”

“I’m familiar with the concept.”

“Well, I wouldn’t want you to get your hands dirty,” Dean said, leaning back as the waiters cleared their plates. 

“I think I’ll be fine, as long as I stay away from your bar.”

Dean glanced down at the formal place settings in faux fascination. “Which fork do I use? I guess I’ll have plenty of time to learn.”

Castiel took a small sip of his water glass. “It’s adorable that you think learning the dinner forks will help you fit in with our family.”

“Oh, Cas. Once Anna and I come into control of her money, your family will be learning to fit in with me.”

“That will be difficult,” Castiel said with a small crease in his brow. “I don’t think we _own_ any banjos.”

Dean shook his head. “No wonder Anna wants nothing to do with you.”

“Our distaste for country music?”

“You’re a bunch of robots. Summer internship at Raven Enterprises?” He scoffed. “It’s like you don’t even know your own sister.”

Castiel tilted his head, a predatory expression in his eyes. “You almost sound as if you care about her.”

“Likewise,” Dean shot back.

He never heard the scathing reply Cas no doubt had ready because Anna and Naomi returned, both looking sick and miserable.

“Everything okay?” Dean whispered to Anna.

“Yeah. Um.” She cleared her throat. Naomi was glaring at her plate, and Castiel was looking back and forth between them, openly curious. “Actually, do you mind if we go for a walk?”

“Of course,” Dean said, shuffling back in his chair.

“I don’t want you to miss dinner -” Anna protested, looking like a kicked puppy.

“Don’t worry about it,” he said, holding out a hand to help her up. “Excuse us.”

“Of course,” Castiel murmured softly.

Anna led them out of the house, down the dark, quiet street. Dean let their shoulders bump, but said nothing.

“She wants me to work for her,” Anna said.

“I heard.”

“She doesn’t care what _I_ want,” Anna said, suddenly angry. “None of them do. It’s all _fall in line_ and _follow orders_ , and eventually it turns us into the next generation of cold, empty -” She sighed, her breath white in the air between them. “You can see them doing it to Cas already. He used to want to get away, and now...”

“Heil Naomi?” Dean asked.

She shivered, and he let his arms come around her, holding her loosely. She sighed into his shoulder.

“This is my fault,” she said.

“What is?”

“Tonight,” she said. “I didn’t prepare you for this, what it would be like.”

“I take it that means I didn’t wow the family?” Dean asked, trying not to sound hopeful.

“You were so nervous,” she sighed. “If only she could see you like _this..._ ”

Something sour twisted in Dean’s gut. Anna tilted her face up to stare at him with her big, hazel eyes. 

“When you’re like this, how could they not love you?” She murmured dreamily.

He swallowed. “Anna -”

She stepped up onto her toes, just enough to press their lips together lightly. A little tingle stole down Dean’s spine, and he tightened his hands on her back. But that sick feeling in his gut wouldn’t go away, and he pulled away after a moment.

“Anna,” he said again.

“What’s wrong?” She asked, eyes still closed.

Her eyelashes looked beautiful against her pale skin, and Dean was always theoretically game for a little necking, but this felt just plain wrong. Aside from all the reasons he hadn’t been dating her in the first place, he was only doing it now to get back at her douchebag brother.

But when she lifted a hand to his cheek, rubbing his scruff gently, it was so warm. It had been so long since someone had touched him like this, like she didn’t want anything beyond the feel of his cheek under her palm. _Only for a few weeks_ , Dean thought, lowering his mouth to hers again, not letting the kiss become more than chaste, comforting. _Not long enough for her to get -_

A clattering sound from down the street had them breaking apart and turning instinctively toward the noise. A small bundle of ratty blonde hair was backing away from the trash can she’d bumped into, shivering and seemingly confused. By her gait it looked like she’d had a few too many, and her clothes were limp and torn, unusual for this neighborhood.

Dean frowned, but Anna was already tugging on his arm, murmuring, “We should go back in.”

He had started to follow her when he heard from behind him, “...Dean?”

It had been years, but he’d know that voice anywhere. He turned, shocked.

_“Jo?”_


	3. Chapter 3

“Jo? What the -” Dean swept her into a hug dazedly. “What are you doing here?”

“I s-stopped by the bar,” she said, in a voice that was too hoarse and dry. Her skin was wan, huge dark circles under her eyes that could have been makeup but probably weren’t. She smelled like a party that’d gone on way too long. Dean held her tighter. “Someone said you were here.” There was a slight twitch in her movements when they finally stepped apart. “Didn’t believe it, but...”

“I -” he struggled for words, before realizing there was an obvious next step. “Anna, this is my - my cousin. Ellen’s daughter, Jo Harvelle. Jo, this is Anna.”

“So nice to meet you,” Anna said warmly.

“Yeah.” Jo’s voice barely carried in the night.

With the introductions over, Dean was back to a loss for words. “I thought - Ellen said you were...” he flailed. “...in New York.”

“Yeah.” She tugged at the hem of her shirt, fidgeting uneasily. “I, um... I left.” A tremulous smile, more of a grimace, passed over her face. “Been clean for a week.”

“Jo, that’s...” He pulled her into another hug, this one considerably more bone-crushing. “How’re you doing? You look... hungry.”

“I could eat,” she admitted with a smile.

“Why didn’t you stay at the Roadhouse?”

The tentative hope that had appeared in her eyes flickered out like a candle in a storm. “Didn’t want to see Mom.”

“Jo,” he intoned, ready to yell, before realizing again that Anna was there. He turned to her, pleading. “Anna, I’m sorry, but I gotta - ”

“Of course,” she said immediately, but then: “Do you - do you want me to come?”

“No,” he said. “You go back in. Make up a good excuse for me.” 

“Okay,” she smiled. She stepped close for another quick kiss on the lips, her eyes open and fixed over Dean’s shoulder as she did so.

When he turned back, Jo was fidgeting again, looking awkward. There was a long pause. 

She frowned at him. “What are you wearing?” 

He pinched her.

*

Several days later, Castiel’s typically quiet morning was interrupted by Zachariah Adler storming into his office, followed closely by Rachel.

“ - don’t think you can just -!” she was shouting, running to put herself between him and Castiel’s desk.

Zach ignored her. “Here he is! My _ally_. A word, Raven?”

“Security are on their way,” Rachel said, glaring up at him.

“Rachel,” Castiel said, silencing both of them. “It’s all right. Please give Mr. Adler and me a moment.”

After Rachel had levelled both of them with a look of deep suspicion, she did as she was told and shut the door behind her. “How can I help you?” Castiel asked blandly.

“Help me?” Zachariah seethed, attempting to loom over Castiel’s desk. “ _Help me?_ You - _charlatan._ ”

“I’m not sure why you’re upset,” Castiel said. “The offer was fair, and you’ll be a millionaire several times over.”

“Oh, yes, what a lovely consolation prize,” Zachariah said. “ _Hostile takeover._ You arrogant bastard - I thought we were on the same side!”

“We’re not,” Castiel said. Zach recoiled. Cas took a sip of his coffee. “But if you’re upset, I’m sure there’s an alternative.”

“Is that so?”

“Yes,” Castiel said. “If you were to hand over all of the debts you hold on the Roadhouse, for example. I think we could come to an agreement.”

Zachariah went completely still. Finally, he said in an uncharacteristically quiet voice: “The Roadhouse?”

“Yes.”

“You’ll let me have my company back for a few tens of thousands worth of debts?” Zach asked, eyes not wide but hard, calculating. “They’re a fraction of what you’d gain through the takeover.”

Castiel said nothing.

“You’re going to pressure Dean,” Zachariah said slowly. “To give up Anna.”

“If that’s true,” Castiel said, “I see no reason for you to hesitate.”

“Yes, of course,” Zachariah said softly, too agreeably. “If you successfully get Anna out of the picture, I’ll have no competition for Dean’s... attention.” His anger had given way to an almost feverish focus on Castiel. “That is, unless, there’s someone new on the scene.”

“You can settle things with Rachel,” Castiel said, opening a new window on his computer. “I should really get back to work.”

There was a long, painful pause before Zach ground out an, “Of course.” But Castiel heard the low murmur of voices outside his office once the door was closed, and sat back in his chair, breathing a sigh of relief.

*

He could make out the screams loud and clear, but not the words. Occasionally he’d catch a bit of something - _disappoint_ , or _not what I said_. He wondered idly if Ellen realized they were opening in less than an hour. The music would cover some of it, but not all, and they weren’t in a position to be scaring customers away with a domestic dispute.

Not that there was a chance in hell he’d actually _intervene._

A light touch to his arm had him jerking around. Anna stared up at him, shocked.

“Sorry,” he said. “Just... um...”

By then she’d heard the shouting, and just slid onto a barstool while shooting him a sympathetic look.

“What’re you doing here?” he asked.

She shrugged. “Realized I’d never come by early before, thought I would see what it’s like.”

He smiled. Her eyes flickered up to the ceiling, where the voices were soaking through the drywall, and back to Dean. “What’re they fighting about?”

Dean sighed. “Jo’s been... hanging out with... not the best crowd,” he hedged. Anna seemed to get it. “She left a while back - almost a year now - and Ellen... it wasn’t good.”

“So... isn’t it good that she’s back? And clean?” Anna asked.

“Yeah,” Dean acknowledged, “but apparently it doesn’t fix everything overnight.”

The shouting stopped abruptly, and the silence was almost worse somehow - it invited thoughts of what they were hissing at each other, what couldn’t be shouted, only whispered across a room. Or worse, what didn’t need to be said at all. 

The shouting picked back up after a moment. “Ellen’s mad that Jo’s crashing here,” Dean sighed.

“Here?” Anna said, eyebrows shooting up. “With you?”

“On my couch, yeah,” Dean said. “She doesn’t think an addict should be living above a bar.”

Anna’s face squinched a little. “She’s not wrong.”

“I know,” Dean said. “But Jo won’t go home. Says she can’t deal with how Ellen...” he trailed off. Anna sat quietly, letting him have the silence. 

“Ellen’s husband, Jo’s dad, he passed a few years ago,” he said eventually. “Bill. Real nice guy. He, uh... got hit by a drunk driver.”

“Ahh,” Anna said quietly, nodding. “I see.”

A loud crash startled them both as Jo came storming into the main floor of the bar and then disappeared just as quickly around the corner. Dean shared a quick look with Anna before they both followed her down into the storeroom.

She paced in the small space, like an animal in a cage. “I can’t -” she was muttering. “I can’t - maybe I shouldn’t have come back here.”

“Don’t say that,” Dean said, holding her lightly by the shoulders - too bony, he could feel straight through her skin like it was wax paper. “We’re over the freaking moon to have you here, Jo. It’s just like old times.”

Her small smile flickered as it passed between him and Anna, hovering in the background. “Ellen’s a hardass, but she loves you,” Dean said.

“I know,” Jo said, head bent and shrugging her shoulders. “I have to accept my own failings.”

“It’ll get easier, Jo,” Dean said, sliding a finger under her chin. “Just gotta hang in there.”

She looked up at him, eyes dark in the shadows. “Do you think -”

“Dean!” A grating bark echoed down the stairs. “Need you up here, stat.”

“Jesus, Crowley, not now,” Dean shot back, irritated.

“I’m afraid it can’t wait,” Crowley said, deigning to stick his head down the staircase. 

“I doubt that.”

“It’s a message from - that businessman you were telling us about.”

Dean’s head snapped around. Crowley looked like he was battling urgency and amusement. “That -” Dean raised his eyebrows, glancing at Anna and then back at him. Crowley nodded. “A message?”

“I told you,” Crowley said, “stat.”

“Uh, Jo, hang on a sec,” he said over his shoulder, bounding up the stairs after Crowley.

Anna made an abortive move to follow him before realizing that would be rude to Jo, who was looking everywhere but at her. Anna dragged a foot in front of her in the awkward silence that followed. 

“Y’know, I -” she started to say, then stopped when Jo’s eyes flew to hers. They were nice eyes, big and surprisingly clear. 

“What?”

“Nevermind,” Anna said, feeling her face heat.

“Okay,” Jo mumbled, going back to staring at the dusty bottles around her. _That_ probably wasn’t good.

“I went through this with my brother,” Anna said, “I was going to say.”

“Yeah?” Jo rasped.

“Yeah,” Anna said. “So I - I know you can beat it.”

Jo scoffed. “That was your brother. You don’t know me.”

“I know Dean,” Anna countered. “I know Ellen. They’re strong. You must be too.”

Jo said nothing for a moment. When she did speak, her voice sounded like it was trying to hide behind her ribs. “Did you hear her yelling at me?” She kept her eyes on the ground. “I’m nothing like her.”

The silence stretched out again, worse this time. Anna took a hesitant step forward.

“My family doesn’t yell,” she said. “We just... talk. Command. Obey. That’s why I love it here.” She took a wistful glance around before turning back to Jo, who was looking at her again. She shrugged ruefully. “Nothing says love like a screaming match.”

“So those happen a lot around here?” Jo asked wryly.

“Well yeah, have you _met_ your family?” Anna teased. She was close enough now to see the threads of bright blonde in Jo’s dark, limp hair. Her eyes were still trained on hers, amused, but with a hint of something else behind them now - like a polaroid picture coming into focus, bleeding into color and form.

“It shows how desperate they are to keep you,” Anna said, and before she knew what she was doing, she had a lock of that soft blonde hair between her fingers, rubbing gently.

Jo’s mouth fell open, breaking the spell. Anna struggled not to stumble backwards. “I - I should go see what has Dean so -”

“Yeah, yeah,” Jo agreed, darting around her to go up the stairs first. Anna followed, head spinning. 

_What the hell was that?_

*

“A letter?” Dean asked, turning it over in his hands. It was thick too, creamy paper adorned in a heavy handwritten script, like it had been done with one of those astronaut pens. Or a quill. “Who sends a letter?”

“Snotty rich bastards,” Crowley replied impatiently. “Open it already!”

It slid open easily, not sealed - messengered over, then. More casual wealth. Dean’s eyes flickered over the contents quickly, and whatever Crowley saw on his face made his own go pale.

“That bad?”

“He has the bills,” Dean said swallowing. “My - the ones from before.”

“Bollocks,” Crowley hissed quietly.

“He’ll foreclose,” Dean said. “If I don’t...”

“Give up Anna?” Crowley supplied.

Dean cursed and tried throwing the paper across the room, which of course failed, enraging him further. “How the hell did he get those bills?” he roared.

“They’re the ones Zachariah had,” Crowley said, having picked up the fluttering missive to eye for himself. “Must’ve given them to him. I bet they play bloody bridge together.”

“He’s not gonna get away with this,” Dean seethed. “I won’t let him.”

“What’s the job, then?” Crowley asked, face lighting up. “A nice thrashing? Kidnapping? Cement shoes?”

“Crowley,” Dean scowled. “Be serious.”

“I am serious,” Crowley said. “He’s threatening your livelihood. Mine too, by extension. What could be more serious than that?”

“We’re not assassinating someone on the Fortune 500 list,” Dean said. “It _might_ get noticed.”

“It’s an odd family,” Crowley argued. “Remember that brother of his, Gavin or something? Been missing twenty-odd years, they still claim he’s hiking the Himalayas.”

“You read too much Teen People,” Dean muttered, grabbing the letter to read again.

“So what,” Crowley said flatly. “Steal Anna away in the night and marry her? Won’t matter if Castiel shuts us down then, we can just reopen in two months.”

“No,” Dean said. “I told you, I’m not taking her money.”

“Well you won’t marry the heiress, you won’t _tell_ Castiel you’re letting him win, and you won’t let me torture him, so I’d love to know what you _are_ going to do!” Crowley fumed, veins bulging in his forehead.

“You’re so tetchy when I don’t let you maim people,” Dean teased.

“Dean,” a sharp voice caught his attention from across the room - Ellen was standing in the doorway, phone cradled against her chest. “Phone for you.”

“Take a -”

“It’s Sam.”

The receiver was cold against his ear. “Sammy?”

“Hey, Dean,” came that familiar voice, strained and awkward but fitting into something in Dean’s chest with only a slight scrape. “Now a good time?”

“Sure, yeah, uh, of course,” Dean said, walking halfway up the stairs to his room for some privacy. “What’s up?”

“Well, I’m, actually, uh, going to be in town tomorrow night.”

“Oh!” Dean said. “Wow, that’s -”

“Short notice, I know. I’m sorry. It’s business, I got pulled into a meeting at the last minute -”

“No, no, it’s great!” Dean said, hating how his voice stole two octaves. “Did you - I mean, do you want to -”

“Yeah, I thought I’d stop by the bar,” Sam said. “Maybe we can have dinner.”

“Yeah, yeah,” Dean said, trying to think of another word, any other word, to use. “That sounds great.” 

There was a pause as Dean tried to think of a way to ask _Ruby’s not coming, is she_ without making Sam cancel the trip altogether before Sam said, “Okay, cool,” and hung up.

Dean was still staring at the phone when Crowley appeared at the foot of the stairs. “Moose coming home, then?”

“Just for a night,” Dean said. “Crap, I have to _clean._ ”

“Hang on a tic,” Crowley said, taking a step up the stairs. “Castiel, remember? What are we going to do?”

“I don’t know,” Dean said. “Sam’s going to be here tomorrow, I have to get this place ready.”

“I don’t think he’s going to wait around for you to give up his little sister,” Crowley said. “We have to -”

“Not now, okay?” Dean said, already turning on the stairs to hurry up to his room.

Crowley waited on the steps, contemplating.


	4. Chapter 4

The problem with the Roadhouse was that the Roadhouse clean didn’t look especially different from the Roadhouse dirty. It was part of its charm, Dean reasoned. Its rustic... down-home... just-folks charm.

As if Sam had ever seen the appeal in anything from their _home._

He bit the inside of his cheek and started polishing the bar again, thinking that maybe if the wood was shiny enough for Sammy to see his damn hair in...

“Uh, Dean?” Ellen asked, leaning into the room.

“Yeah?” He asked without looking up.

“What the hell’s cooking on my stove?”

“Chili.”

“Why does it taste funny?” 

“Vegetarian.”

“Good lord.” She rolled her eyes. “Look at you, selling out to make that boy happy.”

“It’s not that bad,” Dean said. “I put the whole spice rack in there.”

“Lipstick on a - carrot,” Ellen said. “Honey, Sam’s gonna think what Sam’s gonna think, and -”

“Ellen, it’s fine, okay?” He snapped. He made it through re-polishing almost all of the dining room tables before another soft throat-clearing grated on his nerves. “Dammit, Ellen -”

“Down, boy!” Jo said, raising placating hands when he glanced at her. “It’s just me!”

He huffed out an unconvincing laugh. “What do you need?”

“Just checking in on you,” she said.

“Would everyone relax?” Dean said. “So Sammy’s visiting. I’m just making sure the place looks nice, okay?”

“Okay!” Jo said, taking a seat at the next table over. “It looks really nice.”

“Thanks.”

The sound of his washcloth squeaking against the wood filled the silence. “I didn’t think about you much, while I was gone,” Jo said. “I mean - I tried not to. Thinking of home...”

“It’s okay, Jo,” Dean said, looking up at her, trying to temper his stress with something kinder. “I’m not mad, or-”

“No, I just mean,” Jo said, “When I _did_ think of home, I liked to think - well, I hoped you and Sammy had worked it out.”

Dean looked back down at the table. “Yeah. Well.”

“Must be better if he’s visiting, right?” Jo asked.

“Still with that witch,” Dean muttered.

“Sounds like he’s trying, though,” Jo said.

Dean threw the washcloth on the table and pinched the bridge of his nose. “Yeah. It’s a good thing.”

A tap on glass stole his attention - Anna was standing outside the locked front door, peering in under her hand. He threw his washcloth over his shoulder, opened the door a crack, and frowned out at her. “What’re you doing here?”

She glanced briefly over his shoulder to where Jo was still lingering behind the bar. “We had plans. Lunch, remember?”

“Oh,” he said. “Yeah, I’m sorry, something came up.” He gestured behind him. “I have to get the bar ready for tonight.”

“What’s tonight?” she said, gently pushing at his shoulder so she could step inside the bar. “Private party? VIP?”

“Sort of,” he heard Jo say behind him. He turned to glare at her.

Ellen popped her head in behind Jo. “Your, uh, vegan chili was starting to smoke, so I took it off the stove. Think it’s okay though.”

“ _Vegan_ chili?” Anna said incredulously. “You never let me hear the end of ordering salads but you’re making vegan food?”

He knew she was joking, but something about the three female stares on him and the ticking clock in his head made the words itch under his skin like a writhing bug. _"Will everyone just lay off?”_ He snarled.

Anna started and the blood drained from her face. She stared into the corner, as if unsure what to say. Jo was glaring at him, the closest she’d been to her old self since coming back. Ellen raised her eyebrows, unimpressed.

He stormed up the stairs to his room. That’d have to be cleaned too, in case Sammy wanted to see it. He didn’t have time to worry about the women right now.

Anna swallowed, hating the tears that were swimming in front of her eyes. She tried so _hard_ with Dean - to make him laugh, to let him know he could confide in her, to ease some of his burdens. It never worked, and sometimes she just made it worse.

“Hey,” she heard in a soft voice. Jo was looking at her, thankfully with more than just pity in her face. “It’s such a nice day out - you wanna go for a walk?”

“Sure,” Anna said automatically.

The park was riotous with color and soaked up the sun, which turned Jo’s hair that bright blonde again. “Dean’s always been this weird mix of fun and grumpy,” she mused. “Like, he loves music, and horsing around, and scamming on chicks - uh, no offense...” she trailed off awkwardly.

“None taken,” Anna smiled.

“But yeah,” Jo said. “Then he gets the randomest sticks up his ass about nothing. I think it’s an older-brother thing.”

“Yeah...” Anna said tentatively. “What _is_ going on there?”

“I don’t know,” Jo sighed. “I never really got the full story. Sam went to law school, which Dean and John - their dad - were unhappy about for some reason, and then he got some glitzy big firm job in the city, and then he started dating this chick that Dean just _hates_...”

Anna felt her lips twist. “That part’s annoying, but not family-feud bad.”

“I dunno,” Jo said. “I don’t think anyone was prepared for a world where one of us did more than pour drinks or fix cars.” She smiled ruefully. “Or shoot up.”

“Hey,” Anna said, stopping her with a light hand on her shoulder. “You shouldn’t talk about yourself that way.”

Jo’s eyes widened, blinking carefully. “Sorry.”

Anna took a step back, picking up their pace down the trail. “Or Dean. I mean, what he’s done with the bar is really impressive.”

“Of course,” Jo agreed hastily. “It’s a great place.”

They walked in comfortable silence for another few minutes, appreciating the warmth and the freshly-mown grass. It occurred to Anna that she never really sat in silence with Dean - he was always goofing around, flirting with her, telling stories about the bar, trying to guess what new patrons were going to be like. And she was always chasing after his attention with a question or a joke.

“So what’s your story?” Jo asked. “You’re in college, right?”

“Yeah, just finishing up.”

“You know what you want to do?”

“I’m not sure,” Anna said. “My family... well, I kind of feel like I’ve spent my whole life rebelling against something - what they told me to wear, to say, to do. And I’ve realized... I’ve never focused on what I want to _do_. Just what I don’t.”

“I get that,” Jo said, nodding. “But Dean says you’re really smart. You could do anything.”

Anna grinned ruefully. “Anything... everything...” she sighed. “I honestly have no idea. I just know I want to help people.”

Jo smiled. “That’s a good start. I know plenty of people who could use it.”

She looked so vulnerable that Anna bumped her a little on the shoulder, and Jo laughed, staring up into Anna’s face with a shy smile. There was something so different about talking to her- it felt more vital, like Anna was present in their conversation in a way she wasn’t used to. Like Jo was _listening_ to her, eager for what she had to say. 

_It never feels like that with Dean_ , she realized with a sick swoop of her gut. She shook her head, trying to dispel the thought, but it settled into her skin the more she tried to avoid it. And having Jo here by her side just threw it into stark relief - the most she could ever hope to offer Dean was friendship. And she treasured being his friend, knew he’d be there for her if she ever really needed him, but she’d thought - hoped - that they could go deeper than that, come to truly know each other.

But Dean wasn’t getting anything from the friendship beyond company. He always shut himself off, shut her out. 

And Jo opened up like one of the wildflowers in the park.

“So,” Jo said, after a lengthy pause. “You and Dean, huh?”

“Yeah,” Anna agreed vigorously. “Me and Dean. It’s... he’s so great.”

“Yeah, yeah,” Jo nodded.

They’d circled the park, the Roadhouse in view once again. “Back into the breach?” Jo quipped.

Anna tried to smile.

*

Dean’s nose was cold where it pressed against the glass, and he was getting a mark in his forehead from its application to the corner of the window, where he could avoiding being seen from the street.

“Well, this isn’t creepy at all.”

He only jumped slightly at Ellen’s voice, turning to glare. “It’s not. I’m just, y’know...”

“Making sure he doesn’t bolt?” Ellen supplied.

Dean turned to peek out the window again. Sam had been on his phone for twenty minutes now, pacing up and down the sidewalk across the street from the bar, but he hadn’t bailed yet. That had to be a good sign.

“He was nice,” Ellen continued. She’d brought a beer, and was pressing it into Dean’s hand.

“He was polite,” Dean mumbled, staring out the window. Honestly, did Ellen think he couldn’t tell the difference? He’d raised the kid, seen the look on his face when he’d first seen fireworks, when they’d opened their shitty presents Christmas morning, even when he’d gotten a fucking A on his tests. 

Nothing had put that look on Sammy’s face in years except for promotions at that damn firm, and Ruby. It hadn’t been that look tonight when Dean had given him the little tour, even with the Roadhouse sparkling like a new penny. _It’s great, Dean._ Smiling tight and shallow, his approval hovering on the surface, like a damn politician.

It was worse than if he hadn’t come.

“C’mon,” Ellen said, a hand on his shoulder. “No going Glenn Close on me now.”

She steered him into the bar, which did, goddamn it, look pretty good. He’d found a little box of christmas lights to hang up along the windows, giving it a twinkly, big-city look (that Sam should have liked), and Ellen had rounded up enough people to make it pleasantly packed. After enough of Ellen’s poking and prodding he started filling customers’ orders again, though they’d brought in another bartender so Dean wouldn’t have to be working all night and could spend some time with Sammy.

If he ever got off the phone with his demonic girlfriend.

In a corner booth, Anna and Jo were splitting jalapeno poppers and engrossed in conversation. He smiled at the sight. Ellen nudged him in the side. “Didn’t know those two had, ah, bonded,” she said.

“Anna knew you wanted someone to keep an eye on her while she was in here,” Dean said.

“Seems more like they’re just talking,” Ellen said. 

Dean shrugged. “That’s Anna for you.”

Ellen turned an assessing eye on him. “You’re not really this dense, boy. You’re not worried about that?”

“Hell no,” Dean said, not pretending to misunderstand. “That _works_ for me.”

Ellen raised her eyebrows. “Is that so?”

“I been telling you, Ellen. Puppy love.”

She leaned forward, bracing her arms on the bar. “Then why are you so determined to mess with that brother of hers when he could put us out of business?”

Dean gaped incredulously. “Because he’s a dick! He deserves his own special level of hell.”

“Speaking of,” Crowley said, materializing behind them.

A horrible sinking feeling started in Dean’s gut. “Christ, Crowley. What?”

*

_What_ turned out to be Castiel Raven, tied, wrists behind his back, to a wooden chair in the center of their basement storeroom.

Blood trickled from his lip and a cut on his forehead. His expensive suit, now mostly obscured under a long tan trenchcoat, was wrinkled and dusty in the aftermath of whatever the hell had gotten him here. His blue tie was askew. His eyes were thunderous.

“CROWLEY,” Dean roared, turning on the smug little man.

“You’re welcome,” Crowley said.

Before Dean could rip him a new one, Castiel spoke up, voice surprisingly calm. “I’m disappointed, Dean,” he said drily. “I’d thought you above petty subterfuge.”

Dean scowled at him. “Petty _what?_ ”

“Needing to _talk?_ ” Castiel said mockingly, fairly composed for a guy whose arms were pulled taut behind him. “Asking to meet me alone so you could _explain_ , when instead you sent this one and his psychotic bleach-blonde accomplice to assault me.” He sniffed. “A better plan than what I thought was your attempt to appeal to my sympathy, but less elegant than your performance at the gala. You must be desperate.”

“I’m not _desperate_ ,” Dean spat. “And I never asked you to meet me anywhere.”

Castiel’s face was a mask of skepticism. “Yes you did, in several predictably misspelled emails.”

“Bullshit.”

“I’d prove it,” Castiel said, “but I’m tied to a chair.” He gestured to his side.

With a dubious look, Dean knelt in front of Cas to root around in the pocket of his trenchcoat. He half expected the guy to lunge forward and try to bite him or something, but Castiel just sat still, his breath hot but steady, the only sign he felt at all inconvenienced by being trussed up in an enemy’s basement the purse of his thick lips. His eyes stayed on Dean as his fingers closed around Castiel’s phone.

It was unlocked, and finding the emails from 67dean@aol.com was easy. 

_Cass,_

_Cant say in writing, Ill explain everything if u meet me at the park tonite at 8. I promise its importent._

“DAMMIT Crowley!” Dean shouted, growing more pained the further back he read in the chain. “You hacked my damn email?”

“ _Hacked_ is such a specific word,” Crowley said. “There’s a reason you’re supposed to have symbols in your password, _Impala_ was my first guess.”

“Shut up,” Dean said. He turned back to Cas. “You seriously thought I would write this shit?” Castiel shrugged. Dean stood a bit straighter. “Asshole,” he muttered.

“You’re right,” Castiel said, voice dripping sarcasm. “ _I_ was wrong.”

Dean ignored him. “What was your plan, genius?” He asked Crowley. “Keep him here forever?”

Crowley shrugged. “Work him over a bit. Leave him without dinner a few nights. See what it takes to get him to give back the debts.”

“You’re an idiot,” Dean said, and he knelt again to start undoing the ties at Castiel’s ankles. 

Castiel raised his eyebrows. “That’s it? How anticlimactic.”

Dean glared up at him. “Don’t get excited. I’m still gonna destroy you and your family, but I don’t _cheat._ ”

“Of course not,” Castiel drawled. “That would be classless.”

Dean fumed, imagining everything he’d do to a tied-up Castiel if he didn’t have the morals Cas was so sure he lacked. Fear slowly overtook his anger - Crowley was a moron, it’d be a miracle if Castiel didn’t press charges, especially with him all cut and bleeding.

Dean’s fingers froze over the thick polyester rope he didn’t want to know why Crowley owned. _Bleeding._

He glanced up at Castiel. “It’s Thursday.”

Castiel frowned. “So?”

“So tomorrow is Friday,” Dean said, feeling a small smirk tug at his mouth. “Your meeting with your angel investor.”

Castiel’s face slackened in shock, before his eyes narrowed assessingly. “You have a sharp memory.”

Dean’s face heated, but he ignored it. “Unfortunately for you. So, unless you want to miss your meeting and endanger your entire clinic...” He trailed off, standing up and stepping away.

Castiel’s glare was fierce. “You ass.”

Dean laughed. “You got twelve hours to call me all the names you want. After that, I think your poor clinic’s going to be in serious trouble.”

“So much for your pledge not to _cheat_ ,” Castiel said.

Dean clenched his teeth and struggled to keep his fists by his sides. “I don’t think a soulless bastard like you deserves a fair fight.”

“And a bottom-feeder like you deserves to be shut down in disgrace,” Castiel said scathingly. “I’d rather lose the clinic than let you win.”

“You’d let a good cause - as hilarious as it is that you have one - go down?” Dean asked incredulously. “Just to beat me?”

“You seem to have severely underestimated the contempt in which I hold you,” Castiel said with cutting precision.

“No, I was wrong about you wanting to do maybe one good thing in the world,” Dean said, shaking his head in disgust. “But you’re even worse than I thought.”

“This from the kidnapper,” Castiel quipped.

Dean flushed again. “I didn’t kidnap you. But I’ll have no problem letting you _rot_ in here if that’s what you want.”

Castiel’s eyes snapped like an exposed wire. “As opposed to giving you what you want? You’ve made it a very tempting prospect.”

Dean took a long, slow breath. “Suit yourself,” he eventually said, throwing in a shrug just to see Castiel’s eye twitch. “I got nothing better to do all night than flirt with your sister.”

“Indeed,” Castiel said calmly. “That’s all you seem to be good for.”

The thing about a punch to the gut was that it just revved Dean up for the fight to come. He knelt down again to stare Castiel in the eye, heart hammering. “If you weren’t tied up, I’d pound that look off your face.”

Castiel’s lips twitched. “So you have some honor after all.”

“Think it over, Cas,” Dean said, standing and turning his back on him. “I’ll check in on you in a bit.”

“I’ll be here,” Castiel said. 

_Ha ha ha._ “Count on it,” Dean said, and slammed the door behind him.


	5. Chapter 5

Dean had done some weird things during the tenure of their co-ownership of the Roadhouse, but nothing sent a chill of foreboding down Ellen’s spine quite as much as when she went to open the door to the cellar and Dean threw himself in front of it, panting, “Um. Don’t do that.”

Ellen let her eyebrows climb up her forehead very slowly. “Why?”

Dean glanced from side to side. “I. Spilled something on the steps?”

“Boy, you’re a terrible liar,” Ellen said.

“I’m an _awesome_ liar,” Dean countered. 

Ellen waited.

He slumped against the door. “Okay. It’s not a big deal or nothing, Crowley just sort of... kidnapped Castiel and tied him up in the basement so he’d give back the debts.”

Ellen’s heart took a few moments to come back online. “He - _what?_ ”

“ _All you’re good for_ ,” Dean muttered. “He’s the one who offered to pay me. What’s that make him?”

“What in the everloving hell!” Ellen hissed. “He’s actually downstairs?”

“Trussed and angry,” Dean said.

“Have you lost your mind?” Ellen said. There was the faint odor of whiskey on Dean’s breath, but he didn’t seem drunk enough for this to be some kind of hallucination. “He’s going to have us all arrested! Forget the bar, we’ll go to prison!”

“I don’t think he’d do that,” Dean said.

“Why?!” 

Dean frowned thoughtfully. “I don’t know.”

Ellen decided that any time Dean had a look of deep contemplation on his face while a millionaire was tied up in their basement was a good time to start drinking. She was feeling considerably more relaxed when Sam found her half an hour later, sneaking glances at Anna and Jo in the corner and finding herself unable to stop smiling.

“Ellen,” he said, and she smiled at him too. _Big hulking moose._ She liked having Sam around. 

“I like your hair,” she told him.

He laughed. “I don’t usually see you drinking while you’re tending bar,” he said. “Having a good night?”

She barked with laughter. “Not exactly.”

He glanced around. “Why’s that? Place seems great.”

“Oh, it is,” she said. “Except for the billionaire Raven tied up in the basement because Dean is into way kinkier stuff than I ever wanted to picture.”

Sam had taken a step back, his handsome face creased with worry now. “Did you say a Raven?”

“Can’t go a damn hour without saying it these days,” Ellen groused. “Castiel this, Castiel that.”

“ _Castiel_ Raven?” Sam choked. “You have Castiel Raven tied up in your _basement?_ ”

She frowned up at him. “Yeah. Why?”

*

Dean was leaning against a doorframe in the kitchen glaring down the hallway at the storeroom door and nursing a beer when Sam found him, his picture-perfect little bro sweating and agitated. He frowned. “Everything okay?”

“Ellen just told me a funny story,” Sam said, smiling tightly. “Something about a, ah, billionaire tied up in the basement?”

Dean twitched a little, but laughed it off. “Wow, she must’ve gotten hammered.” He tipped his bottle to his brother. “Don’t worry about it, Sammy. I’ve got everything under control.”

Sam went pale. “Oh my god. It’s true? You kidnapped and imprisoned Castiel Raven?!”

“Look, it sounds worse than it is, Sammy –“

“It’s disastrous!” Sammy hissed. “Dean, Jesus Christ, my business meeting? The whale of a client my firm is trying to land? _Castiel Raven!_ ”

It took Dean a moment for this to process. “Huh?”

“Where is it?” Sammy said, coming to loom above him. “The key, the key, give it to me right now!”

“What’re you talking about, the key?” Dean said, backing up against the wall. “You’re seriously here to try to make a deal with Cas?”

“Yeah, and if I do it’ll only put me forward on the partner track about a _year_ , so c’mon, Dean, I can’t mess this up because you’re going through an apparently _really_ weird phase!” Sam was starting to get a maniacal gleam in his eye.

“Hang on a sec,” Dean said. “Don’t you wanna know _why_ I’ve got him locked up? He has the debts on the bar and he’s trying to shut us down!”

“What debts?” Sam asked.

“Uh –” Dean winced. “Shit. I wasn’t going to tell you, but when I took this place over from Dad it wasn’t – we’re not in the best shape, alright? We’re getting there, but dammit, Cas hates me and he’s trying to – he thinks I’m going to marry his sister and steal her money or something, and –“

“So you locked him in a _basement?!_ ” Sam almost shrieked.

“He tried to pay me to leave her, Sammy, he called me a gold-digger!” Dean shouted.

“That doesn’t excuse kidnapping, Dean!” Sam said, and with that he reached forward to try to root through Dean’s pockets. Dean twisted out of his grip and gave him a light thump on the shoulder as a warning more than anything else, but Sam responded instantly, grabbing Dean by the shoulders and throwing him against the wall. They grappled, too close to throw real punches but growing sweaty and bruised by the time Sam wrenched the key away from Dean and backed up, eyes wild.

“What the fuck, Sammy!” Dean roared. “You care more about making partner than your own brother?!”

“I’m doing this for your own good, Dean!” Sam shouted, turning toward the storeroom.

“Oh no you’re – “ But Ellen caught him halfway down the hall.

“Do you have any idea the racket you two are making?” She hissed. “It’s a good night for the bar, we can’t jeopardize that because you two are five-year-olds!”

“Ellen –“ Dean whined, watching Sam fit the key in the lock.

“Let him,” she said lowly. “There’s nothing we can do.”

*

Sam took the stairs two at the time, telling himself that this had to be one of Dean’s funny, funny jokes, and so was somewhat unprepared for the sight of a trenchcoated man, seemingly unperturbed, tied to a chair in the middle of the cellar.

“Oh my god,” Sam said, dropping down in front of him to begin working on the ties. “Mr. Raven, I am so sorry –“

“Who are you?” Castiel asked.

“Sam Winchester,” Sam said, then winced at the thought of how Castiel was probably feeling toward Winchesters at the moment. “Dean’s brother. But I swear, I knew nothing about this, I’m actually in from out of town, when I found out what Dean had done –“

“What is this?” Castiel asked. “Good cop, bad cop?”

“Good – what, no!” Sam said, frowning, redoubling his work on the rope around Castiel’s ankle. “I’m here to let you go! Mr. Raven, you – you have to understand, Dean has always been a little, ah… headstrong, and he doesn’t always think before he –“

“Hold on,” Castiel said, sitting back in his chair as if that would distance himself from Sam. “Has your brother told you why I’m here?”

“Why?” Sam asked, confused. “Well, he – something about bills, I guess, and I think your sister? But obviously there’s no excuse, and I –“

“Your brother told you that I threatened to shut down this bar?” Castiel asked, arching an eyebrow. “Send him and your father into bankruptcy?”

“He –“ Sam stuttered. “Well, yes, I suppose you’re having a, ah, business disagreement –“

“He told you that I insulted him?” Castiel continued. “Insinuated that he was tasteless, stupid, greedy, and cold-blooded?”

Sam swallowed. “Well – I -“

“Knowing all this, you’re here to free me?” Castiel asked.

“Yes!” Sam shouted.

Castiel tilted his head, observing Sam as if he were a species of bug he’d never seen before. “You should be here to give me a black eye.”

“I –“ Sam needed to stand up, pace backwards for a moment, struggling to get a grip on a conversation that was swiftly veering out of his control. “I would never hit someone who was tied up!”

Castiel’s eyes narrowed. “How did you know my name?” He asked. “I’m guessing you didn’t ask your brother while you were, I can only assume, stealing the key.”

“I – I –“ Sam stuttered. “Well the truth is, sir, I, ah – are you familiar with Pellegrino and Boecher?”

Castiel’s eyebrows climbed his forehead. “The law firm?”

“Yes,” Sam said, sighing in relief. “The thing is – I’m sure you’ve forgotten, what with all of this, but we’re actually scheduled to have a meeting tomorrow –“

“Good god, you’re a lawyer,” Castiel mused. “Of course. You’re in town trying to get my business, and that’s why you’re down here pleading your case?”

Sam grit his teeth. “I like to think of myself as opposed to kidnapping in all cases!”

“Okay,” Castiel said. “Well, save your breath. There is not the faintest chance of your firm signing me as a client.”

“Mr. Raven, please,” Sam said. “I told you I didn’t know anything about -”

Castiel laughed at him. “You’d have had a better chance of winning me over if you’d come down here to tighten these ropes.”

Sam’s jaw hung open. “I – what?!”

“I don’t go into business with spineless people.” Castiel spat. “You abomination. Your brother is worth ten of you, and _he’s_ a gold-digger!”

“I – I –“ Sam sputtered. “You… don’t want me to untie you?”

“Certainly not!” Castiel thundered. “Go, lock the door behind you, and give the key back to Dean with my compliments.”

Sam gaped for several minutes before despondently climbing the stairs, locking the door, finding Dean pacing in the corner of the bar, and dropping the key in front of him.

“What the –“ Dean asked, frowning.

“I have to go home for the night.,” Sam said listlessly.

“What happened?” Dean asked, furious. “Did you talk to Cas? Is he gone?”

“He’s still down there,” Sam said, sounding dazed. “Kicked me out. I can’t deal with your weird BDSM shit, Dean. I have to call Ruby. And update my resume.”

“Sam –“

Sam ignored him, left the bar without saying goodbye to anyone else, and hailed a cab while dialing his fiancee’s number.

*

For the second time that evening, Dean was shocked to find Castiel tied up in his basement.

“What the hell?” Dean greeted him, scowling from across the room.

“So far,” Castiel said, seemingly as bored as when he’d last seen him, “I am 0 for 2 with the Winchester family.”

“Did you tell Sam to leave you down here?” Dean demanded.

“Yes,” Cas replied calmly.

“Why?”

The tiniest confused frown creased Castiel’s brow, something above and beyond his usual low-grade allergy to normal people. “He’s more contemptible than you are.” Dean started to object automatically, but Castiel continued: “A battle I can understand, but disloyalty? For a corner office?”

An acknowledging sigh escaped Dean before he could stop it. He stumbled over to a barrel in the corner, letting his head hit the wall behind him as he stared up at the wooden beams. “He’s been off for a while,” he confessed. “He’s so caught up in doing well at that damn firm, and it got even worse when he met this chick who’s just – hey!”

“What?” Castiel asked, perfectly deadpan as Dean leapt to his feet again.

“Is that what this was?” Dean asked. “Trying to get my guard down? Thought I’d let you out if you went all Oprah on me?”

“Please,” Castiel scoffed. “I’m going to beat you fair and square.”

“Uh huh,” Dean said. “What’s your plan for that, exactly?”

“What’s _your_ plan?” Castiel countered. “You’ll let me out of here eventually - you’re no killer, you won’t even hit me while I’m bound. And once I’m free we’ll be exactly where we were.”

“Except you’ll have missed your meeting,” Dean pointed out. “No investor, no clinic.”

Castiel smiled grimly. “I’ll find a way.”

“Mmhm. Why do you need an investor anyway?” Dean asked. “You’ve got all that Raven money. Why not fund the clinic with that?”

Something that looked like vulnerability flashed over Castiel’s face, but it must have been the blinky cellar lighting. “It’s… best not to involve my family,” he said lowly. “Creates less drama.”

“They not as wild about a clinic for poor people as you are?” Dean asked, tilting his face down slightly, trying to catch Castiel’s eye.

“They have other interests.”

“Like saving Anna from me,” Dean pointed out. “You keep your psycho family away from your pet project but do their dirty work on this?”

Castiel met his gaze slowly. “ _I_ wanted to save Anna from you when I realized you were using her for her money.”

And it was so stupid that it hurt, in its antiseptic bluntness, even after all this time - until whatever showed in Dean’s face made Cas’s head tilt, his eyes working like computers, filing away data.

Dean liked that look even less.

He turned to leave. “Dean,” he heard behind him.

“Yeah?”

“If you really don’t intend to torture me,” Castiel said blandly, “do you think you could do me the kindness of a glass of water?”

Dean turned back around so Cas could appreciate his incredulity in full. “A glass of water?”

“Your associate’s ether left me parched,” Castiel announced, face shining with doe-like innocence.

Dean scowled. “Sure, Cas. Why not.”

Upstairs in front of the sink, Crowley appeared behind him, startling the frown off his face. “What’re you doing?”

“What’s it look like?” Dean asked.

Crowley’s glance at the glass in his hand was sharp. “Is that for _Cas?_ ” Dean decided not to dignify him with a response. “What is wrong with you? You’re being sympathetic to the prisoner! This is classic Lima Syndrome!”

“What?”

“The opposite of Stockholm! When a captor falls under the thrall of his captee!”

Dean shut the tap off and brushed past him to the basement. “Don’t think we’re done talking about how creepy it is that you know that. Or that you own _ether_.”

Back downstairs, Dean hovered awkwardly while holding the glass to Cas’s lips, trying not to watch his throat work greedily. When he was done Castiel murmured a polite thank you before returning to his default silent smolder. Dean muttered a few more halfhearted threats, left the glass on one of the shelves, and returned upstairs wondering just what the hell he was doing.

*

By around eleven the bar had thinned out a bit, most of the dinner crowd having left. Jo and Anna had taken up residence at the corner of the bar, heads tilted together as they shared the earbuds of Anna’s ipod.

“This is great,” Jo said a little too loudly even for the roar of the bar, and Dean figured it was as good a time as any to go over and tease them.

Sticking a finger in her ear earned a smack on the shoulder and the beginnings of a lethal Indian burn, so Dean raised his palms and said, “Truce! What’re you kids listening to?”

“This cool indie band Anna likes,” Jo said, smiling broadly and offering him an earbud.

“I’m always telling Dean it’d be good background music for the bar,” Anna said.

Dean grimaced at the sound of tinny electronica rising from the earbud. “No way. You know the rules, Anna, owner picks the music, barflies shut their cakeholes.”

She frowned at him, a frown he couldn’t remember seeing on her face before. “It wouldn’t kill you to try something new.”

“I think it would,” Dean responded seriously. “I think it would literally kill me to listen to one of your Swedish girly-pop bands that dress all in meat or stitched-together tamogatchis.” He ruffled her hair affectionately.

She shrugged out of it, irritated. Jo glanced between them before smiling at Anna. “I think they’re good!”

Anna smiled softly. “But you still prefer Dean’s hair metal.”

Jo sputtered. “I’m only _human._ ”

Anna laughed. Dean liked that look on her face. Ellen came up behind him with big smile to match Anna’s. “What’re we arguing about now?”

Dean started to answer when Castiel came around the corner, sat on a barstool next to Anna, and said, “Could I get a burger, please?”

“Cas!” Anna squealed. “I didn’t know you were coming tonight!”

“Neither did I,” Castiel said calmly, as if Dean wasn’t having a heart attack. “You could almost say I was dragged here.”

“Huh?” Anna asked.

“How d’you want that cooked, Cas?” Dean shouted.

Castiel’s gaze shifted back to his. “Well done.”

“Jo,” Ellen said hoarsely. “Could I talk to you for a second?”

Jo looked confused, but hopped off her barstool. “Sure, Mom. What’s up?”

Ellen pretty much dragged her by the elbow to the back room and up the stairs to Dean’s apartment, Dean’s heart beating in his throat as he watched them go. Anna frowned at their retreating backs. “I’m going to make sure everything’s okay,” she muttered to Cas and Dean, and then left them alone.

The silence was heavy as concrete.

“Wh – what.” 

“I told you I’d win,” Castiel said, reaching out to grab a few peanuts from the nearby bowl. Dean caught a glimpse of bright red at his shirt cuff.

“Jesus,” Dean swore, understanding all at once. “The water glass?”

“Yes, I really needed that. Thank you again, Dean,” Cas said, looking pretty smug for someone who’d apparently sawed himself free with shards of broken glass.

“You look like you tried to off yourself,” Dean said, grabbing for one of his wrists, scowling when Cas squirmed away. “Will you hold on a damn minute, I’m trying to make sure you’re not bleeding out.”

“Yes, your concern for my health is notorious,” Castiel said. “Did you want to tend to my injuries in private, where Crowley can drug me again? I’m not an idiot.”

Dean pointed at a booth in the corner. “I’ll be one minute. Do _not_ leave.”

Castiel looked skeptical, but he was sitting in the booth along with his beer a minute later when Dean emerged from the kitchen with the bar’s first aid kit.

“You’re wily, I’ll give you that,” Dean said. “What, did you kick down the door once you were free?”

“Broke the lock,” Cas said, watching with interest as Dean unpacked antiseptic and gauze. “Or, more accurately, the wood frame around it. Your bar is in shockingly bad shape."

Dean snorted and didn’t reply. Castiel stayed still as Dean rolled his trench and suit cuffs up to expose the jagged though thankfully shallow cuts on his palms and wrists, though he did flinch at the first touch of the medicine. “Serves you right,” Dean commented roughly. “Crazy asshole.”

“So you’re okay with Crowley clubbing me upside the head,” Castiel said, watching Dean gently daub at his skin, “but not with me cutting myself while escaping?”

“Wrists’re, y’know, serious,” Dean said, gesturing with his cotton swab. “And I already told you, I had no idea what Crowley was going to do.”

“You weren’t above using it to your advantage,” Castiel said.

“Yeah, well,” Dean said gruffly. “Never said I was a saint.”

“No, you didn’t,” Castiel murmured.

Dean shot him a dirty look. “Yeah, be as surprised as you want, dick. Of course you thought I’d let you rot in that cellar or bleed to death. If I’d ruin Anna’s life to spite you, why wouldn’t I ruin yours too?”

“So I was wrong about both?” Castiel asked.

Dean’s eyes shot up to his. “No. Of course not.” 

Castiel said nothing, allowing the silence to build up between them again, polluted and angry. Dean wrapped the gauze around Castiel’s wrists slowly, trying not to touch any more of his skin than was strictly necessary. He almost started when he heard Cas’s voice again, low and contemplative. “You must enjoy caring for wounded things.” Dean scoffed, but Cas continued. “Me, this bar. Anna.”

“Anna’s not wounded.” 

“She’s fared better than the rest of us,” he said, and for a crazy second Dean wondered if Cas had ever been young and stupid, crushing on older guys and dreaming about running away from home and being an artist or a groupie or a chef. Probably not. “Caretaking suits you better than combat.” 

“No, it doesn’t,” Dean said shortly. “Don’t think this changes anything - I’m gonna get those bills from you, one way or another.” He frowned. “How did you even know Zach had ‘em? You friends or something?”

Castiel snorted. “Definitely not. He volunteered the information.”

_Wonder why._ Dean’s hands shook as he finished the binding on Castiel’s wrist. “He did, huh? That snake. I shoulda kicked him outta here when he first oiled his way in.”

Castiel twitched his wrist slightly in Dean’s grasp, bringing his eyes up to his again. Cas looked confused. “You didn’t want Zachariah here?”

Anna appeared at their booth. “Cas! What happened?”

Dean’s heart kicked into overdrive, but Cas said merely, “I knocked a glass over and cut myself. Dean was helping.”

Anna’s smile was so warm Dean felt like he was sweating. “He’s helpful, huh?”

“Yes,” Castiel said. “He is.” 

There was an awkward pause. Castiel saved them by brushing his coat off and saying, “If you’ll excuse me, I have an important meeting tomorrow.”

“That’s right!” Anna gasped. “Oh my gosh, Cas, good luck. Do you need anything?”

Castiel leaned over to give her a kiss on the cheek. “Just that.” On his way out Anna smiled at him, and Dean caught him wink at Crowley, who dropped the rag he’d been using to polish the bar.

“Dean,” Anna said, her voice low and worried, “I’m worried about Jo.”

“What?” Dean asked, pulled in too many directions at once.

“Jo,” Anna said impatiently. “Don’t you remember? It was like five seconds ago, Ellen was upset about something, she wouldn’t say what and I think they’re fighting again.”

“Oh,” Dean said, dropping his head into his hands. “No, Anna, I think they’re cool.”

“Being back here is hard on her, Dean, and she needs our support,” Anna said sternly, before giving him a despondent look. “You wouldn’t understand. You don’t need someone to take care of you.”

There was absolutely nothing to say to that, so Dean stood from the booth, gave her a perfunctory hug, and said, “It’s late. You’re doing a great job with Jo. Thanks.” 

He was halfway to his sweet, sweet bed when Crowley caught him by the stairs, murder on his face. “What,” Dean sighed.

“ _What_ what,” Crowley hissed. “Castiel Raven just walked out of here a free man! Are you out of your mind?”

“I didn’t let him out,” Dean said. “He broke out. What was I supposed to do, club him in front of the entire bar?”

“You’re not thinking clearly,” Crowley said. His eyes narrowed. “I think you’ve got a taste for Raven and now one’s not enough.”

“I’m tired, Crowley,” Dean said threateningly. “Let it go.”

Crowley grabbed him by the shirt sleeve. “Are you in love with him?” He demanded.

“Don’t be stupid,” Dean said, shaking free. 

Crowley’s gaze bore into his back as he climbed the stairs to his room.


	6. Chapter 6

Dean’s headache the next morning was distinctly disproportionate to the amount of booze he’d had the night before - just his luck. He treated his symptoms with a greasy omelette and a continual glare at Jo, who was entirely too perky for the crack of noon. Her smile widened further when the front door opened and Anna bounced in like a freaking sunbeam.

“Guess what, guess what?!” She chirruped.

“I left the bar unlocked overnight?” Dean groused.

“I just heard from Cas!” Anna said. Dean scowled against the jolt through his chest. “He’s out of his investor meeting.”

“Yeah?” Jo asked, rapt.

“It went great!” Anna beamed, practically hopping in place. “They’re in, he got the funding, the clinic’s happening!”

Jo’s answering smile was radiant. “That’s amazing!”

“I know! I was a little worried, seeing him here last night,” Anna gushed, sitting down on one of the stools. “I mean, I’m glad he’s loosening up a bit, and that he seems to like the bar, but he is _so_ not the type to get hammered the night before an important meeting. Well, not anymore, anyway. But I should have known he’d pull it together, he’s so smart and resourceful and he always knows how to -”

Dean slammed a fist onto the bar, making his plate rattle loudly. “Can we go one goddamn minute without talking about Castiel?”

Anna’s eyes went big and then small again, not hurt but sad and pitying. Dean left.

Jo’s eyes when she turned them on Anna were luminous. _Beautiful._ “I’m sorry -” She gushed. “It’s Sam, last night, he -”

“It’s okay,” Anna said. She smiled and knew it was wrong, but Jo went with it.

“So - your brother!” She said brightly. “That’s amazing!”

“Yeah! And the best part is, we were talking about it, everything that needs to happen to get it up and running, and he said -” She swallowed nervously, but the look on Jo’s face helped her say: “He offered me a job!”

“A job?” 

“Running the clinic!” Anna said. “Managing it day-to-day, making sure people get the help they need.”

Jo looked shocked but happy. “Wow!”

“I think - I think this is what I want to do,” Anna said hesitantly. “It feels right.”

“Really?”

“Yeah.”

“Well, I think you’d be amazing at it,” Jo said, face brimming with warmth and encouragement. “You’re so smart, so hard-working, and you just - everyone there will _love_ you. I know they will.” 

And then it was like gravity shifted, and Anna couldn’t even stop herself from leaning in, drifting to Jo’s lips like they were the ground beneath her feet. They were soft, and warm, and dry, and she made a tiny sound before opening them, a short, sweet taste that had Anna’s heart pounding. She smelled like salt and eggs and the sun hitting the bar, heating the air around them, and Anna got a hand in that beautiful blonde hair before -

“Oh my god,” Jo gasped, pulling back. “What are we doing?”

Anna’s hands were still grasping her hair and her scratchy jean jacket, and didn’t seem inclined to move. “I don’t know,” she said dumbly, and leaned in again.

“Anna, we can’t,” Jo whispered miserably. “ _Dean._ ”

That finally jolted something like sanity back into Anna’s bloodstream, though it settled sourly in her gut. She blinked at Jo, trying to reconcile what was happening with who she’d been just days ago but could hardly remember now. “I don’t know,” she said, voice hoarse. “We’re... we’re barely even together.”

Jo frowned. “But I thought -”

“He’s been pushing me away for a while,” Anna said. “I thought I was winning him over, but now - I -” she floundered, hating the twisted, confused look on Jo’s face. “I don’t think he’s who I want anymore.”

Jo swallowed and ducked her head. “He’s like a brother to me,” she said. “I can’t do this to him.”

“He deserves the truth,” Anna countered. “He doesn’t have my heart.” She paused, staring into Jo’s eyes like she was falling. “You do.”

And then they kissed and kissed and didn’t stop until Anna nearly lost her balance careening into a barstool and she pulled away again.

“I - we have to - I have to figure out what I’m going to tell Dean."  
"Tell Dean what?" Dean asked, strolling back into the room with a beer and seeming not to notice how Anna and Jo sprang apart like hot potatoes.

"Dean," Anna said, trying to summon her strongest but also most compassionate voice, which probably didn't exist. "We have something to tell you."

"Oookay," Dean said, looking amused. "Shoot."

"I... I -" Anna fumbled. She grabbed Jo's hand for support before thinking better of it, and Dean's eyebrows rose. "This isn't easy, but... Jo and I... we - something's happened."

Dean could tell from the looks on their faces that they thought they were giving him a terminal diagnosis, and he should probably have put them out of their misery immediately, but he'd always been kind of a piece of shit, so instead he turned his back on them and drew in a pained-sounding breath. Anna gasped. "Dean?!"

"You two?" He asked, making his voice dry with pain. "You're... together?"

"I'm so sorry," Anna gushed. “It - it just happened.”

“I can’t believe this,” Dean said, shaking his head. “And - and _Jo._ ”

“I know, I’m so sorry,” Jo said. He thought he heard her take a step forward, but Anna must have stopped her. “You know I would - I would never want to do this to you -”

“My own _sister,_ ” Dean gasped, bringing a drop of condensation from his beer bottle and letting it drip down his cheek before turning back to them. They both went white as a sheet when they saw the faux tear.

“ _Dean!_ ” Jo said. “I - I didn’t think -”

“I can’t believe I finally thought I was ready!” Dean gasped. “Ready... to love!”

There was a long, pregnant pause, before Jo’s horrified expression melted into a scowl and she punched him on the shoulder. He broke into a laugh that had him clutching at his stomach, feeling lighter than he had in days.

“You - what?!” Anna shrieked. 

“You fucker,” Jo said, grabbing his hand to confirm that the tear was from his beer bottle.

“I’m sorry, I couldn’t help it,” he said. “You guys looked so serious.”

“You - you don’t care,” Anna said flatly, and it occurred to him that she might be hurt by his... lack of hurt.

“What can I say,” he shrugged. “I like you two together. And I _told_ you you were never really into me.”

“That’s because you have stupidly low self-esteem,” Anna said. 

Jo beamed at her. “Your loss, Dean.”

“I must have bad taste,” he agreed. “I assume this _just_ happened? I should probably get out of your hair...”

“It’s your bar!” Anna said reluctantly, but Jo was already winding an arm around her waist and drawing her closer, so Dean chuckled and retreated to the back room. He just hoped they wouldn’t do anything to earn him a health code violation.

He found Ellen in the kitchen, opening the mail over a chopping board covered in what looked like onions. He stopped short when he saw a big, thick, ivory envelope at the bottom.

“Oh good, you’re here,” Ellen said drily. “I assume it’s another death threat.”

“You didn’t open it?” Dean said.

“I don’t want any part of that nonsense,” Ellen said. “Jo out there?”

“Yeah, but don’t look,” Dean said vaguely, picking up the envelope.

Ellen frowned. “Why not?”

“Just trust me,” Dean said, and broke the seal. A short, thick sheet of paper slid out along with some older documents. Some very _familiar_ -looking older documents.

“Are those - the bills?” Ellen said, gasping. “The ones Raven had?”

“Can’t be,” Dean rasped, but there they were - in black and white, faded with time and reeking of authenticity. The crisper sheet of paper was a note from Cas.

It said, simply, _For you._

“This is amazing,” Ellen was saying, running her fingers over the faded papers. “We can salvage the bar with these!”

“We can’t _keep_ them,” Dean said. 

“What the - what do you mean we can’t keep them?” Ellen demanded. Crowley walked in.

“Can’t keep what?” he asked.

“Castiel sent over our bills,” Ellen said. “The actual bills, not a threat.”

“What?” Crowley asked, grabbing them from her. “How? Why?”

“I don’t know,” Dean growled. “Which is exactly -”

“You don’t know?” Crowley asked. His sharp eyes went to the note from Cas, still crushed in Dean’s fist. “Really?”

“I’m not gonna be indebted to Cas,” Dean said, ignoring him. “We have to return them, or - or find a way to pay him. With _interest._ ”

“What the hell are you talking about?” Ellen asked faintly. “We don’t have that kind of money, Dean, that’s the point.”

“Yes, Dean,” Crowley said. “It would seem that your Cas has done us a favor.”

Dean flushed. “It’s some kind of play!” he insisted. “C’mon, he’s outmaneuvering us. We have to be smart here.”

“Okay,” Crowley said, too easily. “Time to lock down Anna then?”

“Too late for that,” Dean said without thinking, and Ellen glanced up at the door to the bar, seemingly putting two and two together. Dean winced. Crowley slunk out the back door without another word.

“Dean, what the hell is going on?” Ellen asked him lowly. “You’ve been acting crazed for a while now, and I want to know why.”

“I’m just sick of this shit,” Dean said, glancing down at the pile of paper in mounting panic. Luckily, Jo and Anna chose that moment to burst into the kitchen, holding hands and grinning like maniacs.

“This what I wasn’t supposed to see?” Ellen murmured out the side of her mouth.

“We have a crazy idea,” Anna said, beaming.

“A _really_ crazy idea,” Jo amended.

“Oh lord,” Ellen said. “What now?”

*

Castiel didn’t often leave his office in a good mood, so it was a shame that his unusual light-heartedness lasted only as long as a few steps down the street before he ran into Zachariah.

“Castiel,” the man in question said, smirking like it was carved into his face. “How wonderful that I should run in to you.”

“Is it?” Castiel asked, intending it to be a dismissal as he weaved around him.

“I was just thinking of you,” Zach said, following closely behind. “I’ve heard something I thought you should know.”

Castiel restrained the urge to roll his eyes. “What?”

“It would seem your attempts to save your sister have fallen on deaf ears,” he said, and Castiel stopped abruptly.

“What are you talking about?” he asked sharply.

Zachariah was fishing around in his pocket and brought out his phone, tilting the screen toward Castiel. “One of my colleagues just spotted your sister and Dean Winchester at the courthouse.” He brought up a grainy picture of a redheaded woman and brown-haired man - it could have been Dean and Anna, or it could have been anyone. “They were filing some kind of paperwork. What do you think they were doing?” He asked, obnoxiously rhetorical. “What kind of... _arrangement_ were they establishing?”

Castiel ignored the buzzing in his stomach and the clamminess of his skin and glared at him. “Excuse me, I’m late for a meeting.”

“Sure,” Zach snorted derisively as Cas started walking past him. “You fool. I knew you weren’t strong enough!”

Castiel’s head twitched like a horse trying to shake off a fly. He fumbled for his phone and dialed Anna, hands shaking.

She answered breathlessly, speaking before he had a chance: “Cas! I’ve had the most unbelievable day, you’ll never guess.”

“What,” he managed to croak, the wind whipping cold around his hand.

“ _I got married!_ ” Anna screamed, and Castiel’s world stopped.

“ _What,_ ” he managed again.

“It’s so crazy, we’re still settling everything, and I have to drop Dean back at the bar -” Castiel stumbled on the sidewalk, everything going sideways - “but I’ll explain it all later. Oh my god, I love you, bye!”

She disconnected. Castiel stared at the blank screen in his palm, and curled his fingers around the brittle plastic.

*

He found himself at the bar without entirely knowing how he’d gotten there. They were closed, but a few minutes of curt rapping on the glass brought Ellen to the window, frowning out at him in frank alarm.

“What do you want,” she asked bluntly.

“Is Dean here?”

“Uh, sure, I think he’s in his room, but we’re not open yet -”

“I need to speak with him,” Castiel bit out. “ _Alone._ ”

Ellen’s eyebrows shot up, but she stood aside to let him in. “Uh, okay.”

Dean actually seemed to blush when he first appeared at the top of the stairs, ducking down below the landing to see Castiel. “Hey,” he said, with a tentative smile. He nodded behind himself and Castiel followed him up the stairs, heart racing.

He barely noticed the stacks of books and garbage or the cramped ceiling, though his blood boiled when his eyes flicked over the rumpled bed. Dean closed the door behind them gently, rubbing a hand on the back of his neck and through his hair. _Gorgeous,_ Castiel’s treacherous brain supplied. No wonder he’d had such an easy time luring Anna in. _Destroying_ her. “About the bills,” Dean said.

“Yes, the bills,” Castiel cut in, his voice like glass. “You’ll have no problem paying them now.”

“I -” Dean started, nonplussed. “Well, yeah, I guess -”

“Triumphant is a good look on you,” Castiel said, “but then again everything is. It’s how you survive.”

“What?”

“You’re so _handsome_ ,” Castiel hissed. “And _humble_ \- tending bar, joking around, breaking out the first aid kit. As if there’s anything inside but a worthless, spineless, schemer.”

Dean had gone from confused to appalled to taut with anger. “Hold the fuck on. You’re pissed, I get it, but come on - Anna made her choice, and I don’t think it’s a bad one! A little _fast_ , maybe, but don’t you want her to be happy?”

“Happy?” Castiel shouted. “Happy?! Married to _you?_ ”

Dean went very, very still. “What?”

“Anna’s always talking about how desperate she is to get out of our family because we have no heart,” Castiel spat, the words spilling out of him like acid. “She’s right. We don’t. And for a while I thought she was right about this place too, that you -” 

There was something soft in Dean’s eyes, but Castiel remembered the glee in Anna’s voice. “But you’re empty, through and through. Nothing but a whore.”

An ugly, set grimace had taken over Dean’s face. “What can I say, Cas. I told you from the start there was nothing you could do to save her from me.”

“You were right,” Castiel said. “You ruined Anna the moment you put your ring on her finger.”

Dean jabbed a hand into his pocket and pointed the other at Castiel. “Save it, Cas. It’s over now, all your threats and schemes and _buyouts_. You’re right, I won and you lost. Guess you’re not as smart as you thought you were.”

Castiel laughed. “And you turned out to be much simpler than I thought you were. You still have no idea how much you’ve really lost, do you?” He took a swaggering step forward, drunk on the challenge in Dean’s eye. “That if you’d played your cards more cleverly, you would have had an even bigger fortune than Anna’s to waste on this bar, an even more powerful name to wield on your behalf?”

Dean’s wide eyes were so close. “What are you talking about?”

He took another step forward, watching Dean’s adam’s apple bob. He smelled so good. _This is crazy._ “You, Dean Winchester, master manipulator, didn’t guess?” Cas murmured. His manic smile faded slowly at the confused fury twisting Dean’s face, the heavy breaths he was drawing, his eyes so green and clear. “That’s hilarious,” he muttered. “I’ll give thanks every night to have so narrowly avoided making the worst mistake of my life.”

“Get out,” Dean said, voice shaking. “Get out.”

“Gladly,” Castiel said, leaving without another word.

Dean was still leaning against the wall when Ellen found him. “What the hell happened? I heard yelling.”

“Is he gone?” Dean asked hoarsely. 

“Yeah,” Ellen said, brow furrowed in that achingly familiar way.

Dean felt himself sliding down the wall, strings just cut. For some reason that seemed to worry Ellen more than the yelling. “What? What is it? Do you need Jo? Crowley? _Sam?_ ” 

“No,” Dean cut in harshly. “Don’t bother Jo, or Sam, and I sure as shit don’t need Crowley. Just -” he paused, realizing he was still having trouble catching his breath. “Pour me a shot.”

Ellen frowned, but ran downstairs for the bottle.


	7. Chapter 7

While Castiel occasionally felt ridiculous about having agreed to let Naomi’s interior decorator loose on his apartment, he had to admit that the uniform white and chrome mod-ness of it made a stereotypically perfect place to brood. There were no curtains, so the blackness of the night stared back at him from all angles, floor to ceiling. An uninterrupted view of nothing.

He slumped in his chair and stared into the miniature faux fire, his foot tapping absently on the tile floor, vestigial energy whose target was long-gone. In such a short time he’d become so used to having a purpose, an agenda to his day beyond the typical corporate hellscape. _Outsmart Dean. Anticipate Dean’s next move. Dean Dean Dean._

This would probably be just like the drugs. _It feels horrible now,_ he thought, _but I’ll detox, and then... I’ll be myself again._ Factory reset. Debugging. Just like last time.

The front door slammed and he heard Naomi should his name. _A security system,_ he thought tiredly. _That’s what would complete this cliche._

Naomi rounded his chair, all righteous indignation. “Castiel! Have you heard?”

He didn’t look at her. “Yes.”

“My god,” she said. “I can barely believe it.”

“I’m sorry,” he said, leaning back and closing his eyes. “I failed.”

“ _You_ failed?” She asked. “I don’t think anyone saw this coming.”

That got him to crack an eyelid irritatedly. “What are you talking about? It’s been coming for weeks, and I thought -” He shook his head. “But I was wrong.”

“Weeks?” Naomi demanded, equally confused. “What are you talking about?”

“Dean!” Cas said, befuddled and angry. “He’s won. He convinced Anna to marry him, just as we feared.”

“Dean?” Naomi asked, dripping scorn. “Dean Winchester? Castiel, are you back on drugs? Anna has married his _cousin_. A _woman_. Jo Harvelle!” 

He abruptly found himself out of the chair and looming over Naomi. “What are you talking about?”

“So you didn’t know,” Naomi said, with a delicate lift of her eyebrows. “I can’t blame you; it came out of absolutely nowhere, and I told Anna so. But she thinks she’s _in love!_ Disgraceful.”

He grabbed Naomi’s arms and fought the urge to shake. “What are you talking about?!”

“Anna’s wife!” Naomi shouted, starting to look concerned. “She just came to town a week ago, apparently. Anna actually _bragged_ to me about her being a recovering addict, as if that’s something to be _proud_ of. _She’s so strong, mother!_ Honestly. She’s such a child, marrying someone she’s only known for days. And you just know it’s a phase, something she’s doing merely -”

Cas was done listening. “I have to leave.”

“But wait! I came here to strategize with you,” Naomi said. “I think we can get the marriage annulled somehow - it’s so soon, and this Harvelle woman being an addict works in our favor -”

“I have no interest in attacking Anna’s marriage,” Castiel said, jerking his trenchcoat on roughly. “And I plan on never meddling in another of our family’s affairs again.”

Naomi frowned. “What’s gotten into you, Castiel?”

“I’ve made a huge mistake, and I have to correct it.” He just prayed that Dean would listen.

“Castiel!” Naomi cried plaintively behind him. He ignored her.

*

The bar was packed, which was good, because it meant sales and also that Dean didn’t have to think about anything or talk to anyone. It didn’t stop Ellen from giving him _searching_ looks under the tickets as he shouted into the kitchen, but those were easy to ignore.

In the seething mass of bodies, it took him a full second to realize that the flash of tan fabric he’d seen whipping through the door was him.

He swallowed, hating the tension in his gut. Castiel was moving differently than he normally did - not so compact and controlled tonight. His dark head whipped around the bar, frenzied, clearly searching for -

Dean’s heart lurched when those eyes met his, and Cas immediately started for him. He was aware of an embarrassing desire to just run, but he held his ground, letting only disdain into his voice when he said, “Get out of my bar, asshole.”

Castiel stopped a few feet away, stricken. _“Dean.”_

“Out,” Dean repeated, since Cas didn’t look like he’d gotten the message.

Cas pressed his body against the bar, leaning as close as he could. “I’m going to say what I’m going to say,” he said lowly, “and I think you’d rather I not say it in front of this entire bar.”

They were already getting a few curious glances, so Dean took a deep breath and said, “Fine,” lifting the hatch and beckoning Cas back, toward the kitchen.

Ellen and the guys on staff that night looked at him like he’d gone bonkers when he barked at them to get out, but he wasn’t doing this in the damn cellar and he sure as shit wasn’t inviting Cas up to his bedroom again. Plus with all the boilers going it was hot - hopefully that’d make this quick.

Cas didn’t beat around the bush once they were alone. “Dean,” he said again, in that intense, urgent voice, “I’ve come to - to _beg_ your forgiveness.” 

“Figured out I wasn’t the asshole your sister married, huh?”

“I’m...” Cas swallowed, as off-balance as Dean had ever seen him. “I was misinformed. Misled. I jumped to conclusions, and I’m sorry.”

“Save it, Cas,” Dean said. “I don’t even know why you’re here. Aside from being cousins-in-law, we have nothing to do with each other anymore.”

Something besides guilt shone in Castiel’s face, something intent and possessive. “I was only that upset about you marrying Anna because - because - ...”

The silence punched a stung laugh out of Dean. “You can say it when you’re about to take a swing at me, but not now?”

“I -” He faltered through it, blinking rapidly and swallowing. “I’ve come to care about you - very deeply...” 

“You have a hilarious way of showing it,” Dean said, though he couldn’t quite manage a smile.

Castiel huffed, frustrated. “I’m sorry, Dean! I’m not Anna, this has never come easily to me.”

“What?” Dean asked incredulously.

Castiel looked as if he was so confused and surprised and pissed off at the world and mostly Dean for not getting it that he was two seconds from tearing that ruffled hair out. _“People.”_

One second Dean was staring at him, trying to decide if that was the flat-out worst romantic declaration slash apology he’d ever heard, and the next they were kissing, Cas soft but insistent in pushing him back into a rattling shelf of cans. It made no sense, because Cas couldn’t be both the cold untouchable asshole Dean had been battling and the guy stealing every angry thought out of Dean’s head with his hot tongue curling inside Dean’s mouth, but he was. Solid and real under Dean’s hands, breathing hotly onto Dean’s face, making the lowest little desperate noises that set Dean’s blood on fire -

Dean shoved him away, panting and hating himself. “Get the fuck off me. Don’t touch me.”

Cas looked stricken, even more confusing with his lips all red. “I’m sorry. Dean, please.”

“Please what? Fix you?” 

Cas blanched, and Dean shook his head, tireder than he’d ever been. “No.”

Cas blinked and his face shuttered. He stood up straighter, shaking his shoulders out. “Yes. Of course. I’m... sorry for bothering you.”

He left Dean alone with the boiling pots and the sound of snapping grease.


	8. Chapter 8

Anna squealed when she saw Castiel in her doorway, dropping the several hundred dresses she was trying to squeeze into her one pathetic duffel bag.

“I’m very happy for you,” he choked out in the middle of a backbreaking hug.

“Thanks,” she said, finally pulling back. “I’m sorry there wasn’t a real wedding, I know it was a bit impulsive...”

“Don’t apologize,” Castiel told her. “More foolish things have been done in the name of love.”

Anna gave him a sharp look, but drifted back to the gigantic pile of dresses. “Where are you two heading?” He asked.

“The Grand Canyon,” Anna said happily. “Jo’s always wanted to go, and I’d never been. Road trip!”

Castiel smiled faintly. “That sounds nice. Do we own any properties...?”

“Nope,” Anna said. “We’re staying in some crappy little motel. Jo’s choice.” She beamed. “It’s going to be amazing!” 

“You do love experiencing _real_ life, don’t you?” He teased.

“It’s not like that,” she said, face falling. “I’m not... _slumming._ ”

“I know. I didn’t mean -”

“Jo, Dean, Ellen - they’re more alive than anyone in our family, present company excluded,” Anna said. “Maybe Dean and I weren’t right for each other, but being a part of their family is. Everything doesn’t always have to be perfect. They’re allowed to make mistakes. They’re free.”

“Are they?”

Anna frowned. “What do you mean?”

Cas sat on a corner of her bed, suddenly tired. “Why is Dean running that bar?”

Anna bit her lip and stared down at him sadly. “Cas... what happened?”

He covered his eyes with a hand. “I don’t want to talk about it.”

“Cas...”

He smiled up at her before she could continue. “I meant it, Anna. I’m very happy for you. You’ve always been smarter than me, but I’m ashamed it took me this long to realize you’re stronger, too.”

She tilted her head, considering him carefully. “And I always took for granted how strong you are.”

He took a deep breath. “Don’t stay away too long. The clinic needs its director.”

“Oh, I’ll be back!” She said, with a twinkling smile. “I just need a week or so to absolutely _wreck_ my wife.”

Castiel grimaced.

*

“Aside from the fact that if you do that one more goddamn time I’m going to rip that thing outta your hands and shove it where the sun don’t shine -” Ellen said, appearing in his doorframe.

Dean only jumped a little. “Good morning to you too.”

“ - you are the dictionary definition of mopey, sitting up here alone. With your _ball_ ,” Ellen finished, scowling.

Dean threw the little rubber ball against the wall again and caught it, mostly out of spite. “Shut up.”

“Come downstairs,” Ellen wheedled. “Have lunch with me.”

“Not hungry.”

“Oh, _that’s_ not worrying.” When it became clear Dean had decided not to validate that with a response, she said, “Sam called again.”

“Yeah?” He asked, keeping all interest out of his voice. 

“Sounded pretty upset.”

“Yeah, well.” Dean groused. “I think Cas ruined his week too.”

“No, it was something about that girl you hate.” Dean’s head jerked up. “Sounds like she might be on the way out.”

“Really?” He hated how stupidly hopeful he sounded.

“Call your brother,” Ellen said. “I think he needs you.”

“I... I will.”

He waited until Ellen had left before digging around for his phone, which he’d been ignoring in case - at any rate, before he could pull up Sam’s number, he saw a voicemail from Crowley, and some niggling little suspicion had him listening to it first.

_“Dean. It’s breaking pretty much every rule I’ve got to be calling you beforehand, but you’ve been such a mess these last few days I couldn’t resist the chance to give you a little pick-me-up. It’s Castiel Raven -”_ Dean choked a little and missed a good second or two - _“...punish him for the stunts he’s pulled on us. As I speak my team is laying the groundwork for a pretty nasty surprise at that new clinic you were talking about - when these beauties go off it won’t be a slightly run-down hospital so much as a hole in ground. See how much he needs to invest to fix_ that _. So chin up, darling. As always, I’ve got your back.”_

Dean tripped on the stupid rubber ball scrambling to get some clean clothes from his dresser.

*

Everyone in town knew where Raven HQ was, though Dean did have something of a hard time explaining to the front desk guy just why he needed to see the almighty Castiel Raven _right now_. So it was an awesome coincidence that Cas chose that moment to get off the elevator and stare at Dean in shock. “Dean?”

“Cas -” Dean gasped, uncaring of the strange looks he was getting from the other buttoned-up businesspeople. “I gotta talk to you -”

“Of course,” Cas said, leading him into some kind of conference room on the ground floor and shutting the doors behind them firmly. He immediately went to a side table that was decked out with breakfast snacks and poured a glass of water.

“What are you doing?” Dean asked, impatient.

“You look upset,” Castiel said, offering him the glass.

“I’m fine, it’s - it’s Crowley,” Dean said. “He, uh, y’know, was helping me with -”

“Defeating me, yes,” Castiel said drily. “What of him?”

“I just got a message - I think he’s planning on blowing up your clinic,” Dean blurted. “Or, the site, or something -” he bent over, suddenly aware of how fast he was breathing, “Christ, I thought you might be there right now -”

“Dean, sit down,” Cas said, his voice full of annoyingly misplaced concern.

“Cas, aren’t you listening, we gotta call the cops -”

“Dean. The police arrested four men attempting to break into the clinic last night,” Castiel said. “I didn’t ask for names, but I’m assuming that Crowley was among that group?”

_Oh._ It finally occurred to Dean to check the timestamp of Crowley’s voicemail: 1AM last night. Of course, he wouldn’t be laying down c4 or whatever in broad daylight. “Oh thank god,” Dean said, and sat down on some kind of fancy bench, taking the glass of water from Cas and chugging it. Cas sat beside him, watching carefully. 

When Dean was done he wiped his mouth with his sleeve, put the glass down, and said, “I should go.”

“You can rest for a minute. You’re shaking,” Cas said, one of his hands twitching up off the bench and then settling down. “Did you run over here?”

“I was... worried.”

“You could have called,” Cas said, voice soft so it wasn’t a jibe. “Or called the police yourself.”

“Yeah, well,” Dean muttered. “Now I’m... sure.”

“Sure of what?”

Dean stared at him and couldn’t answer. Cas’s eyes flicked to his lips and back before he leaned in and kissed him softly, too softly. Dean didn’t make any move to respond, but didn’t push him away either. He was just so tired, and it felt good, really good, like something inside him unwinding, _breathing,_ after so, so long. Things had started to get embarrassingly warm considering they’d barely opened their lips when he finally broke away. “Cas, we can’t.”

“Why not?” he murmured.

“For one thing, you’re still an asshole.”

“I apologized,” Cas breathed, leaning in again.

Dean groaned at a grazing, open kiss to the side of his mouth. “And you’re a presumptuous motherfucker.”

“I just know how to push an advantage,” he replied, sliding a hand up Dean’s thigh.

“Wait,” Dean said. “The bills...”

“Keep them.”

“No! I’m paying you back.”

“Actually, I was thinking of investing in your bar,” Cas said, now nibbling on Dean’s ear.

Dean sighed, aiming for indignant but coming out a little breathy. “You’ve gotta be kidding me.”

“I’m very serious.”

“But what if someone _else_ from your family comes by to try to stop me and I end up making out with them instead -”

Cas kissed him again, like he had before, and there were several long silent minutes interrupted only occasionally by a voice in Dean’s head wondering just how much the people in the lobby could see through the mesh blinds over the windows and then deciding _oh, whatever._


End file.
